JP6985829B2 - Pigment composition, coloring composition and coloring curable composition - Google Patents

Description

The present invention relates to pigment compositions, coloring compositions and coloring curable compositions.

The color curable composition is used in the manufacture of a color filter used in a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display. The color-curable composition may contain two or more colorants having different colors in order to obtain a desired color tone or the like.

For example, Japanese Patent Application Laid-Open No. 2015-19767 (Patent Document 1) describes a colored photosensitive composition for a green color filter as described in C.I. I. Pigment Green 7 and C.I. I. Pigment Yellow 129 and C.I. I. It is described that it contains at least one yellow pigment selected from the group consisting of Pigment Yellow 139.

Japanese Unexamined Patent Publication No. 2015-197677

The present inventors have stated that a cured film formed from a color-curable composition containing a phthalocyanine-based colorant and a yellow colorant may cause a decrease in brightness when a light resistance test in which light is continuously irradiated is carried out. It became clear by the examination.

［式（Ｉ）中、Ｌ¹は、−ＣＯ−又は−ＳＯ₂−を表す。
Ｒ¹〜Ｒ⁵及びＲ¹²〜Ｒ¹³は、互いに独立に、水素原子、−ＣＯ−Ｒ¹⁰²、−ＣＯＯ−Ｒ¹⁰¹、−ＯＣＯ−Ｒ¹⁰²、−ＣＯＣＯ−Ｒ¹⁰²、−Ｏ−Ｒ¹⁰²、−ＳＯ₂−Ｒ¹⁰¹、−ＳＯ₂Ｎ（Ｒ¹⁰²）₂、−ＣＯＮ（Ｒ¹⁰²）₂、−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯ−Ｒ¹⁰²、−ＮＨＣＯ−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯＯＲ¹⁰²、−ＯＣＯＮ（Ｒ¹⁰²）₂、ハロゲン原子、シアノ基、ニトロ基、−ＳＯ₃Ｍ、−ＣＯ₂Ｍ、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｒ²とＲ³、Ｒ³とＲ⁴、Ｒ⁴とＲ⁵及びＲ¹²とＲ¹³は、それぞれ互いに結合して環を形成してもよい。
Ｒ¹¹及びＲ¹⁰¹は、互いに独立に、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｒ¹⁰²は、水素原子、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｍは、水素原子又はアルカリ金属原子を表す。
Ｒ¹⁰¹、Ｒ¹⁰²及びＭが複数存在する場合、それらは同一であってもよく、異なっていてもよい。
波線は、Ｅ体又はＺ体を表す。］
［２］ 式（Ｉ）で表される化合物が、式（Ｉ−ａ）で表される化合物である［１］に記載の顔料組成物。

［式（Ｉ−ａ）中、Ｌ¹、Ｒ¹¹、Ｒ¹〜Ｒ⁵及び波線は、前記と同じ意味を表す。
Ｌ²は、−ＣＯ−又は−ＳＯ₂−を表す。
Ｒ¹⁴は、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。］
［３］ Ｒ¹¹とＲ¹⁴とが同じ基であり、Ｌ¹とＬ²とが同じ基である［２］に記載の顔料組成物。
［４］ Ｒ¹¹及びＲ¹⁴が、互いに独立に、置換基を有していてもよい炭素数１〜４０のアルキル基、置換基を有していてもよいフェニル基、置換基を有していてもよいナフチル基、置換基を有していてもよいテトラヒドロナフチル基、置換基を有していてもよいチエニル基、置換基を有していてもよいフリル基又は置換基を有していてもよいピリジニル基である［２］又は［３］に記載の顔料組成物。
［５］ 式（Ｉ）で表される化合物が、式（Ｉ−ｂ）で表される化合物である［１］に記載の顔料組成物。

［式（Ｉ−ｂ）中、Ｌ¹、Ｒ¹¹、Ｒ¹〜Ｒ⁵及び波線は、前記と同じ意味を表す。
Ｒ²⁰及びＲ³⁰は結合して環Ｑを形成する。
環Ｑは、置換基を有していてもよく、環の構成員数が５〜７の環であり、該環Ｑは、炭化水素環でもよく複素環でもよい。環Ｑには、炭化水素環及び複素環から選ばれる、環の構成員数が５〜７の単環又は該単環が縮合した縮環が結合してもよい。］
［６］ 式（Ｉ）で表される化合物が、式（Ｉ−ｃ）で表される化合物である［５］に記載の顔料組成物。

［式（Ｉ−ｃ）中、Ｌ¹、Ｒ¹¹、Ｒ¹〜Ｒ⁵及び波線は前記と同じ意味を表す。
Ｒ⁶及びＲ⁷は、互いに独立に、水素原子、−ＣＯ−Ｒ¹⁰²、−ＣＯＯ−Ｒ¹⁰¹、−ＯＣＯ−Ｒ¹⁰²、−ＣＯＣＯ−Ｒ¹⁰²、−Ｏ−Ｒ¹⁰²、−ＳＯ₂−Ｒ¹⁰¹、−ＳＯ₂Ｎ（Ｒ¹⁰²）₂、−ＣＯＮ（Ｒ¹⁰²）₂、−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯ−Ｒ¹⁰²、−ＮＨＣＯ−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯＯＲ¹⁰²、−ＯＣＯＮ（Ｒ¹⁰²）₂、ハロゲン原子、シアノ基、ニトロ基、−ＳＯ₃Ｍ、−ＣＯ₂Ｍ、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環を表す。
Ｒ¹⁰¹、Ｒ¹⁰²及びＭは、前記と同じ意味を表す。］
［７］ Ｒ¹が水素原子であり、Ｒ²〜Ｒ⁵が、互いに独立に、水素原子又はニトロ基である［１］〜［６］のいずれかに記載の顔料組成物。
［８］ ［１］〜［７］のいずれかに記載の顔料組成物及び溶剤を含む着色組成物。
［９］ さらに、樹脂を含む［８］に記載の着色組成物。
［１０］ さらに、式（Ｉ）で表される化合物、黄色着色剤又は緑色着色剤を含む［８］〜［９］のいずれかに記載の着色組成物。
［１１］ ［８］〜［１０］のいずれかに記載の着色組成物及び重合性化合物を含む着色硬化性組成物。
［１２］ さらに、重合開始剤を含む［１１］に記載の着色硬化性組成物。
［１３］ ［８］〜［１２］のいずれかに記載の着色組成物又は着色硬化性組成物から形成されたカラーフィルタ。
［１４］ ［１３］に記載のカラーフィルタを含む液晶表示装置。
［１５］ 式（Ｉ）で表される化合物と、
キノフタロン化合物、式（Ｉ）で表される化合物以外のイソインドリン化合物または緑色着色剤を含む顔料組成物と、溶剤と、着色剤（Ａ２）及び溶剤を含む着色剤（Ａ２）含有液とを、混合する着色組成物の製造方法。

［式（Ｉ）中、Ｌ¹は、−ＣＯ−又は−ＳＯ₂−を表す。
Ｒ¹〜Ｒ⁵及びＲ¹²〜Ｒ¹³は、互いに独立に、水素原子、−ＣＯ−Ｒ¹⁰²、−ＣＯＯ−Ｒ¹⁰¹、−ＯＣＯ−Ｒ¹⁰²、−ＣＯＣＯ−Ｒ¹⁰²、−Ｏ−Ｒ¹⁰²、−ＳＯ₂−Ｒ¹⁰¹、−ＳＯ₂Ｎ（Ｒ¹⁰²）₂、−ＣＯＮ（Ｒ¹⁰²）₂、−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯ−Ｒ¹⁰²、−ＮＨＣＯ−Ｎ（Ｒ¹⁰²）₂、−ＮＨＣＯＯＲ¹⁰²、−ＯＣＯＮ（Ｒ¹⁰²）₂、ハロゲン原子、シアノ基、ニトロ基、−ＳＯ₃Ｍ、−ＣＯ₂Ｍ、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｒ²とＲ³、Ｒ³とＲ⁴、Ｒ⁴とＲ⁵及びＲ¹²とＲ¹³は、それぞれ互いに結合して環を形成してもよい。
Ｒ¹¹及びＲ¹⁰¹は、互いに独立に、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｒ¹⁰²は、水素原子、置換基を有していてもよい炭素数１〜４０の炭化水素基又は置換基を有していてもよい複素環基を表す。
Ｍは、水素原子又はアルカリ金属原子を表す。
Ｒ¹⁰¹、Ｒ¹⁰²及びＭが複数存在する場合、それらは同一であってもよく、異なっていてもよい。
波線は、Ｅ体又はＺ体を表す。］
［１６］ 着色剤（Ａ２）が、式（Ｉ）で表される化合物、緑色着色剤、及び黄色着色剤から選ばれる１種以上の着色剤である［１５］に記載の製造方法。 The present invention includes the following inventions.
[1] The compound represented by the formula (I) and
A pigment composition containing a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green colorant.

[In formula (I), L ¹ represents −CO− or −SO _2−.
R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
R ¹¹ and R ¹⁰¹ represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.
The wavy line represents an E-body or a Z-body. ]
[2] The pigment composition according to [1], wherein the compound represented by the formula (I) is a compound represented by the formula (Ia).

[In the formula (Ia), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
L ² represents −CO − or −SO _2−.
R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. ]
[3] The pigment composition according to [2], wherein ^{R 11} and R ¹⁴ are the same group, and L ¹ and L ^{2 are the same group.}
[4] R ¹¹ and R ¹⁴ have an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, and a substituent independently of each other. It has a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, and a frill group or a substituent which may have a substituent. The pigment composition according to [2] or [3], which is also a good pyridinyl group.
[5] The pigment composition according to [1], wherein the compound represented by the formula (I) is a compound represented by the formula (I-b).

[In the formula (I-b), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ²⁰ and R ³⁰ combine to form a ring Q.
The ring Q may have a substituent and has 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocycle. A single ring having 5 to 7 ring members or a condensed ring obtained by condensing the single ring, which is selected from a hydrocarbon ring and a heterocycle, may be bonded to the ring Q. ]
[6] The pigment composition according to [5], wherein the compound represented by the formula (I) is a compound represented by the formula (I-c).

[In the formula (I-c), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ⁶ and R ⁷ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ^101. , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON ( R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group or a substituent having 1 to 40 carbon atoms which may have a substituent. Represents a good heterocycle.
R ¹⁰¹ , R ¹⁰² and M have the same meanings as described above. ]
[7] The pigment composition according to any one of [1] to [6], ^{wherein R 1} is a hydrogen atom and R ^{2 to} R ^{5 are independent of each other as a hydrogen atom or a nitro group.}
[8] A coloring composition containing the pigment composition and the solvent according to any one of [1] to [7].
[9] The coloring composition according to [8], which further comprises a resin.
[10] The coloring composition according to any one of [8] to [9], further comprising a compound represented by the formula (I), a yellow colorant or a green colorant.
[11] A coloring curable composition containing the coloring composition according to any one of [8] to [10] and a polymerizable compound.
[12] The color-curable composition according to [11], which further comprises a polymerization initiator.
[13] A color filter formed from the coloring composition or the coloring curable composition according to any one of [8] to [12].
[14] A liquid crystal display device including the color filter according to [13].
[15] The compound represented by the formula (I) and
A pigment composition containing a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green colorant, a solvent, and a colorant (A2) -containing liquid containing the colorant (A2) and the solvent. A method for producing a coloring composition to be mixed.

[In formula (I), L ¹ represents −CO− or −SO _2−.
R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
R ¹¹ and R ¹⁰¹ represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.
The wavy line represents an E-body or a Z-body. ]
[16] The production method according to [15], wherein the colorant (A2) is one or more colorants selected from a compound represented by the formula (I), a green colorant, and a yellow colorant.

The present invention provides a pigment composition, a coloring composition and a coloring curable composition that can be used for forming a color filter having improved light resistance.

The pigment composition of the present invention comprises a compound represented by the formula (I) (hereinafter, may be referred to as a compound (I)), a quinophthalone compound, an isoindolin compound other than the compound represented by the formula (I), or an isoindrin compound. Contains with green colorants.
Compound (I) also includes its tautomers and salts thereof.
Compound (I) can be used as a colorant.
The pigment composition of the present invention may contain one kind or two or more kinds of compounds (I).
Isoindoline compounds or green colorants other than the quinophthalone compound and the compound represented by the formula (I) can be used as the colorant.
The pigment composition of the present invention may contain one or more quinophthalone compounds, an isoindoline compound other than the compound represented by the formula (I), or a green colorant.
The pigment composition of the present invention may contain a colorant other than the compound (I) and the quinophthalone compound (hereinafter, may be referred to as a colorant (A1-1)).
The pigment composition of the present invention may contain a colorant other than the compound (I) and the isoindoline compound other than the compound (I) (hereinafter, may be referred to as a colorant (A1-2)).
The pigment composition of the present invention may contain a colorant other than the compound (I) and the green colorant (hereinafter, may be referred to as a colorant (A1-3)).
The coloring composition of the present invention contains a compound (I), a pigment composition containing a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green coloring agent, and a solvent (E). Further, the pigment composition containing the compound (I), the quinophthalone compound, the isoindoline compound other than the compound represented by the formula (I), or the green colorant is preferably dispersed in the solvent (E).
The coloring composition of the present invention may contain a resin (hereinafter, may be referred to as a resin (B)).
The coloring composition of the present invention may contain a coloring agent (hereinafter, may be referred to as a coloring agent (A2)).
The colorant (A2) may contain one kind or two or more kinds of colorants.
The colorant (A2) preferably contains compound (I), a yellow colorant or a green colorant.
Further, the color-curable composition of the present invention is a pigment composition containing the compound (I), an isoindoline compound other than the quinophthalone compound, the compound represented by the formula (I), or a green colorant, the solvent (E) and the solvent (E). Contains the polymerizable compound (C).
The color curable composition of the present invention may contain a polymerization initiator (D).
The color curable composition of the present invention may contain a polymerization initiation aid (D1).
The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.

<Compound (I)>
The compound (I) is a compound represented by the formula (I).

[In formula (I), L ¹ represents −CO− or −SO _2−.
R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
R ¹¹ and R ¹⁰¹ represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.
The wavy line represents an E-body or a Z-body. ]

In the present specification, the wavy line represents an E-form or a Z-form, and specifically, the wavy line represents an E-form, a Z-form, or a mixture thereof.

R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ^101. , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , hydrogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, It is preferable to represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

L ¹ is preferably −CO−.

The ^{hydrocarbon groups represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² have 1 to 40 carbon atoms, preferably 1 to 30, more preferably 1 to 20 carbon atoms. , More preferably 1 to 15, and even more preferably 1 to 10.

The hydrocarbon groups having 1 to 40 carbon atoms represented by R ^{1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may be aliphatic hydrocarbon groups or aromatic hydrocarbon groups.} Often, the aliphatic hydrocarbon group may be saturated or unsaturated, or may be chain or alicyclic.

Saturated or unsaturated chain hydrocarbon groups represented by R ^{1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include methyl group, ethyl group, propyl group, butyl group and pentyl group. , Hexyl group, Heptyl group, Octyl group, Nonyl group, Decyl group, Undecyl group, Dodecyl group, Heptadecyl group, Octadecyl group, Icosyl group and other linear alkyl groups; isopropyl group, isobutyl group, sec-butyl group , Tart-butyl group, (2-ethyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl) pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, ( Branched chain alkyl groups such as 3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group, and (3-ethyl) heptyl group; vinyl group, 1-propenyl Group, 2-propenyl group (allyl group), (1-methyl) ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1- (2-propenyl)) ethenyl group, (1) , 2-Dimethyl) alkenyl groups such as propenyl groups and 2-pentenyl groups; and the like. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, still more preferably 1 to 15 carbon atoms, and even more preferably 1 to 10 carbon atoms. Even more preferably, it is 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ^{1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include cyclopropyl group, 1-methylcyclopropyl group and cyclobutyl group. , Cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group , 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3 , 5-Dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6 , 6-Tetramethylcyclohexyl group and cycloalkyl group such as 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group; cyclohexenyl group (eg cyclohexenyl group) -2-ene, cyclohexa-3-ene), cycloalkenyl groups such as cycloheptenyl group, cyclooctenyl group; norbornan group, adamantyl group, bicyclo [2.2.2] octane and the like can be mentioned. The alicyclic hydrocarbon group preferably has 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, still more preferably 4 to 15, and even more preferably. Is 5 to 15, particularly preferably 5 to 10. Of these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

The ^{aromatic hydrocarbon groups represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a phenyl group, an o-tolyl group, an m-tolyl group, and a p-tolyl group. 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4- Vinyl phenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4 -Ethylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6-bis (2-propyl) phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl Group, 4-vinylphenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group , Aromatic hydrocarbon groups such as phenyl group and anthryl group, pyrenyl group; and the like.
The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 15.

The ^{aromatic hydrocarbon groups represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² are the above-mentioned hydrocarbon groups (for example, aromatic hydrocarbon groups and chain hydrocarbons). It may be a group in which at least one of a hydrogen group and an alicyclic hydrocarbon group) is combined, and is an aralkyl group such as a benzyl group, a phenethyl group, a 1-methyl-1-phenylethyl group; a phenylethenyl group (phenyl). Arylalkenyl group such as (vinyl group); arylalkynyl group such as phenylethynyl group; phenyl group to which one or more phenyl groups such as biphenylyl group and terphenylyl group are bonded; cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl (phenyl) ) Methyl) Phenyl group and the like.
The ^{groups represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² are the above-mentioned hydrocarbon groups (for example, chain hydrocarbon groups and alicyclic hydrocarbon groups). ), For example, cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl. It may be an alkyl group to which one or more alicyclic hydrocarbon groups such as a group and an adamantylmethyl group are bonded.
The carbon number of these groups is preferably 4 to 30, more preferably 6 to 30, still more preferably 6 to 20, and particularly preferably 6 to 15.

The ^{hydrocarbon groups represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have a substituent. The substituent may be monovalent or divalent. For the divalent substituent, it is preferable that two bonds are bonded to the same carbon atom to form a double bond.
As the monovalent substituent,
Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, Octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group , O-triloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group , 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6- Dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group , 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, etc., and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a group represented by the following formula, or a derivatizing group thereof. (For example, a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably an octyl sulfamoyl group), or the like). Oxy group bonded to one side;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl) hexylthio group, heptylthio group, octylthio group, nonylthio group, decylthio group, undecylthio group, dodecylthio group, icosylthio group. A sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a group, a phenylthio group and an o-tolylthio group is bonded;

Epoxy group, oxetanyl group, tetrahydrofuryl group, tetrahydropyranyl group;
Formylation group;
Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanol group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyle group, octanoyl group, nonanoyl group, decanoyle group, undecanoyl group, dodecanoyl group, A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, etc.) such as a henicosanoyl group and a benzoyl group, and a group represented by the following formula. A carbonyl group (the carbonyl) to which a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like is bonded) is bonded. When the group is an alkanoyl group, the number of carbon atoms is preferably 2 to 12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl) hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group Group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc., and represented by the following formula A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), a carbon, etc. An oxycarbonyl group to which a group derived from an alkylsulfamoyl group (preferably an octylsulfamoyl group) having a number of 1 to 10 is bonded;

アミノ基；
Ｎ−メチルアミノ基、Ｎ，Ｎ−ジメチルアミノ基、Ｎ−エチルアミノ基、Ｎ，Ｎ−ジエチルアミノ基、Ｎ−プロピルアミノ基、Ｎ，Ｎ−ジプロピルアミノ基、Ｎ−イソプロピルアミノ基、Ｎ，Ｎ−ジイソプロピルアミノ基、Ｎ−ブチルアミノ基、Ｎ，Ｎ−ジブチルアミノ基、Ｎ−イソブチルアミノ基、Ｎ，Ｎ−ジイソブチルアミノ基、Ｎ−ｓｅｃ−ブチルアミノ基、Ｎ，Ｎ−ジｓｅｃ−ブチルアミノ基、Ｎ−ｔｅｒｔ−ブチルアミノ基、Ｎ，Ｎ−ジｔｅｒｔ−ブチルアミノ基、Ｎ−ペンチルアミノ基、Ｎ，Ｎ−ジペンチルアミノ基、Ｎ−（１−エチルプロピル）アミノ基、Ｎ，Ｎ−ジ（１−エチルプロピル）アミノ基、Ｎ−ヘキシルアミノ基、Ｎ，Ｎ−ジヘキシルアミノ基、Ｎ−（２−エチル）ヘキシルアミノ基、Ｎ，Ｎ−ジ（２−エチル）ヘキシルアミノ基、Ｎ−ヘプチルアミノ基、Ｎ，Ｎ−ジヘプチルアミノ基、Ｎ−オクチルアミノ基、Ｎ，Ｎ−ジオクチルアミノ基、Ｎ−ノニルアミノ基、Ｎ，Ｎ−ジノニルアミノ基、Ｎ−フェニルアミノ基、Ｎ，Ｎ−ジフェニルアミノ基、Ｎ，Ｎ−エチルメチルアミノ基、Ｎ，Ｎ−プロピルメチルアミノ基、Ｎ，Ｎ−イソプロピルメチルアミノ基、Ｎ，Ｎ−ブチルメチルアミノ基、Ｎ−デシルアミノ基、Ｎ，Ｎ−デシルメチルアミノ基、Ｎ−ウンデシルアミノ基、Ｎ，Ｎ−ウンデシルメチルアミノ基、Ｎ−ドデシルアミノ基、Ｎ，Ｎ−ドデシルメチルアミノ基、Ｎ−イコシルアミノ基、Ｎ，Ｎ−イコシルメチルアミノ基、Ｎ，Ｎ−ｔｅｒｔ−ブチルメチルアミノ基、Ｎ，Ｎ−フェニルメチルアミノ基等、及び以下の式で表される基等の１つ又は２つの炭素数１〜２０（好ましくは炭素数１〜１０）の炭化水素基又はその誘導化基（例えばカルボキシ基、スルホ基、ニトロ基、ヒドロキシ基、ハロゲン（好ましくは塩素原子）、炭素数１〜１０のアルキルスルファモイル基（好ましくはオクチルスルファモイル基）等で誘導化された基）で置換されたアミノ基；

Amino group;
N-methylamino group, N, N-dimethylamino group, N-ethylamino group, N, N-diethylamino group, N-propylamino group, N, N-dipropylamino group, N-isopropylamino group, N, N-diisopropylamino group, N-butylamino group, N, N-dibutylamino group, N-isobutylamino group, N, N-diisobutylamino group, N-sec-butylamino group, N, N-disec-butyl Amino group, N-tert-butylamino group, N, N-ditert-butylamino group, N-pentylamino group, N, N-dipentylamino group, N- (1-ethylpropyl) amino group, N, N -Di (1-ethylpropyl) amino group, N-hexylamino group, N, N-dihexylamino group, N- (2-ethyl) hexylamino group, N, N-di (2-ethyl) hexylamino group, N-Heptylamino group, N, N-diheptylamino group, N-octylamino group, N, N-dioctylamino group, N-nonylamino group, N, N-dinonylamino group, N-phenylamino group, N, N -Diphenylamino group, N, N-ethylmethylamino group, N, N-propylmethylamino group, N, N-isopropylmethylamino group, N, N-butylmethylamino group, N-decylamino group, N, N- Decylmethylamino group, N-undecylamino group, N, N-undecylmethylamino group, N-dodecylamino group, N, N-dodecylmethylamino group, N-icosylamino group, N, N-icosylmethylamino Group, N, N-tert-butylmethylamino group, N, N-phenylmethylamino group, etc., and one or two groups represented by the following formula, etc. 1 to 20 carbon atoms (preferably 1 carbon group) 10) hydrocarbon group or derivatizing group thereof (eg, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsul). Amino group substituted with a group) derivatized with a famoyl group) or the like;

Sulfamoyl group;
N-methylsulfamoyl group, N, N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N, N-diethylsulfamoyl group, N-propylsulfamoyl group, N, N-dipropyls Rufamoyl group, N-isopropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N, N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N, N-diisobutylsulfamoyl group, N-sec-butylsulfamoyl group, N, N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N, N-ditert-butylsul Famoyl group, N-pentylsulfamoyl group, N, N-dipentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N, N-di (1-ethylpropyl) sulfamoyl group, N-hexyl Sulfamoyl group, N, N-dihexyl sulfamoyl group, N- (2-ethyl) hexyl sulfamoyl group, N, N-di (2-ethyl) hexyl sulfamoyl group, N-heptyl sulfamoyl Group, N, N-diheptyl sulfamoyl group, N-octyl sulfamoyl group, N, N-dioctyl sulfamoyl group, N, N-octylmethyl sulfamoyl group, N-nonyl sulfamoyl group, N, N-dinonyl sulfamoyl group, N-phenyl sulfamoyl group, N, N-diphenyl sulfamoyl group, N, N-ethylmethyl sulfamoyl group, N, N-propylmethyl sulfamoyl group, N, N-isopropylmethylsulfamoyl group, N, N-butylmethylsulfamoyl group, N-decylsulfamoyl group, N, N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N , N-undecylmethylsulfamoyl group, N-dodecylmethylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N, N-icosylmethylsulfamoyl group, One or two carbon atoms 1 to 20 (preferably carbon) of N, N-tert-butylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group, etc., and a group represented by the following formula, etc. A hydrocarbon group having a number of 1 to 10) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), and an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably). Induced by octylsulfamoyl group) etc. Sulfamoyl group substituted with (ta);

Formylamino group; acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanolamino group, pentanoylamino group, hexanoylamino group, (2-ethyl) hexanoylamino group, heptanoyle Amino group, octanoylamino group, nonanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, etc., and a group represented by the following formula. Etc., a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), 1 carbon atom). A carbonylamino group (preferably a group derivatized with an alkylsulfamoyl group (preferably an octylsulfamoyl group) of 10 to 10) is bonded (when the carbonylamino group is an alkanoylamino group, the number of carbon atoms is preferably 1. ~ 12);

Hydroxy group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Carboxy group, -CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); sulfo group, -SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro group Cyan group;
Formyloxy group; acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group Carbon such as a group, an octanoyloxy group, a nonanoyloxy group, a decanoyyloxy group, an undecanoyloxy group, a dodecanoyloxy group, a henicosanoyloxy group, a benzoyloxy group, etc., and a group represented by the following formula. A hydrocarbon group having a number of 1 to 20 (preferably 1 to 10 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), and 1 to 10 carbon atoms). A carbonyloxy group to which an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) or the like is bonded (when the carbonyloxy group is an alkanoyloxy group, the number of carbon atoms is preferably 1 to 10). be);

メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、ブチルスルホニル基、ペンチルスルホニル基、ヘキシルスルホニル基、（２−エチル）ヘキシルスルホニル基、ヘプチルスルホニル基、オクチルスルホニル基、ノニルスルホニル基、デシルスルホニル基、ウンデシルスルホニル基、ドデシルスルホニル基、イコシルスルホニル基、フェニルスルホニル基及びｐ−トリルスルホニル基等、及び以下の式で表される基等の炭素数１〜２０（好ましくは炭素数１〜１０）の炭化水素基又はその誘導化基（例えばカルボキシ基、スルホ基、ニトロ基、ヒドロキシ基、ハロゲン（好ましくは塩素原子）、炭素数１〜１０のアルキルスルファモイル基（好ましくはオクチルスルファモイル基）等で誘導化された基）が結合したスルホニル基；

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl) hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, un A decylsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, etc., and a group represented by the following formula having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms). A hydrocarbon group or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably an octyl sulfamoyl group)). Sulfonyl group to which a group induced by etc.) is bound;

Carbamic group;
N-methylcarbamoyl group, N, N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N, N-diethylcarbamoyl group, N-propylcarbamoyl group, N, N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N , N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N, N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N, N-diisobutylcarbamoyl group, N-sec-butylcarbamoyl group, N, N-disec- Butylcarbamoyl group, N-tert-butylcarbamoyl group, N, N-ditert-butylcarbamoyl group, N-pentylcarbamoyl group, N, N-dipentylcarbamoyl group, N- (1-ethylpropyl) carbamoyl group, N, N-di (1-ethylpropyl) carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N, N-di (2-ethyl) hexylcarbamoyl group , N-Heptylcarbamoyl group, N, N-diheptylcarbamoyl group, N-octylcarbamoyl group, N, N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N, N-octylmethylcarbamoyl group, N, N-octyl Butylcarbamoyl group, N, N-dinonylcarbamoyl group, N-phenylcarbamoyl group, N, N-diphenylcarbamoyl group, N, N-ethylmethylcarbamoyl group, N, N-propylmethylcarbamoyl group, N, N-isopropyl Methylcarbamoyl group, N, N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N, N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group , N, N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N, N-icosylmethylcarbamoyl group, N, N-tert-butylmethylcarbamoyl group, N, N-phenylmethylcarbamoyl group and the like, and the following. A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group) such as a group represented by the above formula. , A carbamoyl group substituted with a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.;

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluorooctyl group, perfluorononyl group, Carbonation of 1 to 20 carbon atoms in which all hydrogen atoms such as a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group are substituted with a fluorine atom. Hydrogen group;
Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, perfluoro A linear chain having 1 to 20 carbon atoms in which all hydrogen atoms such as nonylmethyl group, perfluorodecylmethyl group, perfluoroundecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group are substituted with fluorine atoms. Alternatively, a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of the branched chain;
1 to 20 carbon atoms (preferably carbon number) in which a part of hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine. Hydrocarbon groups 1 to 10);
-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₂ carbon atoms -CH _3, etc. 20 (preferably having 2 to 10 carbon atoms) bound to an alkyl group as bonded to a thiocarbonyl _{group, -CO-S-C 6 H} 5 aryl group having 6 to 20 carbon atoms, such as the Thioketone group;
* -COCO-R as represented by the following formula (in the formula, R is a hydrogen atom and a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above, R satisfies 1 to 20 carbon atoms). , Or its inducing group (eg, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)). Group of));

_{* -NRCONR 2} as represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above, those satisfying 1 to 20 carbon atoms). ), Or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. Groups derived from), the Rs of which may be the same or different from each other, or bonded to each other to form a ring);

以下の式で表されるような＊−ＯＣＯＮＲ₂（式中、Ｒは水素原子、炭素数１〜２０の炭化水素基（例えば上記に挙げられる炭化水素基のうち炭素数１〜２０を満たすもの）、又はその誘導化基（例えばカルボキシ基、スルホ基、ニトロ基、ヒドロキシ基、ハロゲン（好ましくは塩素原子）、炭素数１〜１０のアルキルスルファモイル基（好ましくはオクチルスルファモイル基）等で誘導化された基）であり、該Ｒは互いに同じでもよく異なっていてもよく、互いに結合して環を形成していてもよい）の基；

_{* -OCONR 2} as represented by the following formula (in the formula, R is a hydrogen atom and a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above, those satisfying 1 to 20 carbon atoms). ), Or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. Groups derived from), the Rs of which may be the same or different from each other, or bonded to each other to form a ring);

* -NRCOOR as represented by the following formula (in the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above, those satisfying 1 to 20 carbon atoms)). , Or an inductive group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like. Derivatized groups), the Rs of which may be the same or different from each other, or bonded to each other to form a ring) groups;

* -OP (O) (OCH ₃ ) _{2 and the} like * -OP (O) (OR) ₂ (In the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, the hydrocarbon group listed above). Of these, those satisfying 1 to 20 carbon atoms), or their inducing groups (eg, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms). (Preferably a group derivatized with an octylsulfamoyl group) or the like), and the Rs may be the same or different from each other, or may be bonded to each other to form a ring).
_{* -Si (CH 3) 3,} * - Si (CH 2 CH 3) 3, * - Si (C 6 H 5) 3 and _{* -Si (CH (CH 3)} 2) 3 etc. * -SiR ₃ ( In the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, one of the above-mentioned hydrocarbon groups satisfying 1 to 20 carbon atoms), or a derivatizing group thereof (for example, a carboxy group or a sulfo group). A group derived from a group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.). The groups may be the same or different from each other, and may be bonded to each other to form a ring); and the like.

As the divalent substituent, an oxo group, a thioxo group, an imino group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an aryl group having 6 to 20 carbon atoms are substituted. Examples include the imino group. Examples of the imino group substituted with the alkyl group include CH ₃ −N =, CH ₃ −CH ₂ −N =, CH ₃ − (CH ₂ ) ₂ −N =, CH ₃ − (CH ₂ ) ₃ −N =, and the like. Can be mentioned. Examples of the imino group substituted with the aryl group include C ₆ H _5- N = and the like.

Preferred examples of the substituent of the hydrocarbon group having 1 to 40 carbon atoms include the substituent of the group s1. The inducing group shown below is a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like. It is preferably an derivatized group.
[Group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof bonded to one side;
A carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof is bonded;
An oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof is bonded;
Amino group;
An amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivatizing group thereof;
Sulfamoyl group;
A sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivatizing group thereof;
A carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof is bonded;
Hydroxy group;
Halogen atom;
-CO ₂ M (preferably a carboxy group); (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom).
-SO ₃ M (preferably a sulfo group); (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom).
Nitro group;
Cyano group;
A carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof is bonded;
A sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatizing group thereof is bonded;
Carbamic group;
A carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivatizing group thereof;
A hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are replaced by fluorine atoms;
A hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms have been replaced by a linear or branched alkyl group having 1 to 20 carbon atoms;
A hydrocarbon group having 1 to 20 carbon atoms in which a part of a hydrogen atom is replaced by fluorine;
Oxo group;
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, a substituent of group s2 is more preferable.
[Group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof bonded to one side;
A carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded;
An oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded;
Amino group;
An amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatizing group thereof;
Sulfamoyl group;
A sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatizing group thereof;
A carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded;
Hydroxy group;
Fluorine atom, chlorine atom, bromine atom;
-CO ₂ M (preferably a carboxy group); (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom).
-SO ₃ M (preferably a sulfo group); (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom).
Nitro group;
Cyano group;
A carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded;
A sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded;
Carbamic group;
A carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatizing group thereof;
A hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are replaced by fluorine atoms;
A hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms have been replaced by a linear or branched alkyl group having 1 to 10 carbon atoms;
A hydrocarbon group having 1 to 10 carbon atoms in which a part of a hydrogen atom is replaced by fluorine;
Oxo group;

Hydrocarbon groups having 1 to 40 carbon atoms having substituents represented by R ^{1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 have monovalent or divalent substituents.} Examples thereof include hydrocarbon groups having 1 to 40 carbon atoms, preferably saturated or unsaturated chain hydrocarbon groups having 1 to 30 carbon atoms having monovalent or divalent substituents, and monovalent or divalent substituents. A saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms or a group combining an aromatic hydrocarbon group or a hydrocarbon group having 6 to 30 carbon atoms having a monovalent or divalent substituent. Examples thereof include groups having 1 to 30 carbon atoms having a monovalent or divalent substituent.
More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1 and a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1. , A group having a substituent of group s1 and having 6 to 20 carbon atoms or a combination of an aromatic hydrocarbon group or a hydrocarbon group, and having a substituent of group s1 having 1 to 20 carbon atoms can be mentioned.
Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2 and a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2. , A group having a substituent of group s2 and having 6 to 15 carbon atoms or a combination of an aromatic hydrocarbon group or a hydrocarbon group, and examples thereof include a group having a substituent of group s2 and having 1 to 15 carbon atoms.

The ^{heterocyclic group represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may be monocyclic or polycyclic, and is preferably a ring. It is a heterocycle containing a heteroatom as a component. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, still more preferably 3 to 20, even more preferably 3 to 18, and even more preferably 3 to 3. It is 15, and particularly preferably 3 to 14.

As a heterocycle containing a nitrogen atom,
Monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, piperazine;
Pyrrole such as 2,5-dimethylpyrrole, pyrazole such as 2-methylpyrazole and 3-methylpyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole and other 5-membered cyclic unsaturated heterocycles. ;
Pyrimidines such as pyridine, pyridazine, 6-methylpyrimidine, 6-membered ring-based unsaturated heterocycles such as pyrazine, 1,3,5-triazine;
Quinoxaline such as indazole, indolin, isoindolin, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro (3-methyl) quinoxaline, 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, diazanaphthalene. , Purine, pteridine, benzopyrazole, benzpiperidin and other fused bicyclic heterocycles;
Condensed tricyclic heterocycles such as carbazole, acridine, and phenazine; and the like.

As a heterocycle containing an oxygen atom,
Monocyclic saturated heterocycles such as oxylan, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, 1-cyclopentyldioxolane;
Bicyclic saturated heterocycles such as 1,4-dioxaspiro [4.5] decane and 1,4-dioxaspiro [4.5] nonane;
Lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone;
Five-membered ring-based unsaturated heterocycles such as furan such as 2,3-dimethylfuran and 2,5-dimethylfuran;
6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran;
Benzopyrans such as 1-benzofuran and 4-methylbenzopyran, condensed bicyclic heterocycles such as benzodioxole, chroman, and isochroman;
Condensed tricyclic heterocycles such as xanthene and dibenzofuran; and the like.

As a heterocycle containing a sulfur atom,
A 5-membered ring-based saturated heterocycle such as dithiolane;
6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, 2-methyl-1,3-dithiane;
Five-membered ring-based unsaturated heterocycles such as thiophene such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran such as 4H-thiopyran and benzotetrahydrothiopyran;
Condensation bicyclic heterocycles such as benzothiophene;
Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

As a heterocycle containing a nitrogen atom and an oxygen atom,
Monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone;
Monocyclic unsaturated heterocycles such as oxazoles such as 4-methyloxazole, 2-methylisoxazoles, and isooxazoles such as 3-methylisoxazole;
Fused bicyclic heterocycles such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxan, benzoimidazoline;
Condensation tricyclic heterocycles such as phenoxazine; and the like.

As a heterocycle containing a nitrogen atom and a sulfur atom,
Monocyclic heterocycles such as thiazoles such as 3-methylthiazole and 2,4-dimethylthiazole;
Condensation bicyclic heterocycles such as benzothiazole;
Condensation tricyclic heterocycles such as phenothiazine; and the like.

The heterocycle may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group.
Other heterocycles may be represented by the following groups.

Further, the heterocyclic group may be a heterocyclic group formed by bonding two or more of ^{R 1 to} R ^5. Such a heterocyclic group has a ring structure of two or more rings together with a benzene ring to which ^{R 1 to} R ^{5 are bonded.} Examples of the ring structure having two or more rings include the structure of the following formula.

The binding site of the above heterocycle is a portion where an arbitrary hydrogen atom contained in each ring is eliminated.

The ^{heterocyclic group represented by R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have a substituent. Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} When the heterocycle contains a nitrogen atom as a constituent element thereof, the hydrocarbon group mentioned above may be bonded to the nitrogen atom as a substituent.
The preferred substituent is the same as the preferred substituent that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Things can be mentioned.
Examples of the heterocyclic group having a substituent represented by R ^{1 to R 5} , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a heterocyclic group having a monovalent or divalent substituent. , Preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s2.

The above-mentioned hydrocarbon group or heterocyclic group may have one or more substituents (first substituents), and the two or more substituents are independent of each other. It may be the same or different.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group contained in a part thereof. The second substituent can be selected from the same groups as the first substituent.
Hereinafter, -CO-R ¹⁰² of ^{R 1 ~R 5, R 12,} R 13, -COO-R 101, -OCO-R 102, -COCO-R 102, -O-R 102, -SO 2 -R 101 , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCON (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰²⁾ ) ₂ , Halogen atom, -SO ₃ M, -CO ₂ M will be described.
-CO-R ¹⁰² includes formyl group; acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanol group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyle group, octanoyl group, nonanoyl. A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a group, a decanoyl group, an undecanoyl group, a dodecanoyl group, a henicosanoyl group, a benzoyl group, etc., and a group represented by the above formula. It was derivatized with a chemical group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like. A carbonyl group to which a group) is bonded (when the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) and Tables 1 to 8, Table 9 (a), Table 9 (b) and Table 10 to Table 10. Among the compounds shown in Table 11 and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290, the groups corresponding to ^{-CO-R 102 are mentioned in the compounds excluding the compounds shown in Tables 10 to 11 below.} More preferably, a carbonyl group to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or an inductive group thereof is bonded (when the carbonyl group is an alkanoyl group, the number of carbon atoms is more preferably 2). ~ 12), and in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11 ^{below, the groups corresponding to -CO-R 102} and the like can be mentioned. ..
-COO-R ¹⁰¹ includes a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, and a (2-ethyl) hexyloxycarbonyl group. Heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc., and represented by the above formula. A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or an inducing group thereof (for example, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), carbon An oxycarbonyl group to which an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) of the number 1 to 10 is bonded and Tables 1 to 8, Table 9 (a) and Table 9 (b). ) And the compounds shown in Tables 10 to 11 and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290, excluding the compounds shown in Tables 10 to 11 below, correspond to ^{-COO-R 102.} Examples thereof include a group, more preferably an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded, and Tables 1 to 8, Table 9 (a) and Table 9 (b) below. In addition, in the compounds shown in Tables 10 to 11, ^{the groups corresponding to −COO-R 102} and the like can be mentioned.
-OCO-R ¹⁰² includes formyloxy group; acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl). Hexanoyloxy group, heptanoyleoxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henikosanoyloxy group, benzoyloxy group, etc., and the above formula. A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by (preferably a chlorine atom) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, or a halogen (preferably a chlorine atom). ), A carbonyloxy group to which an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like is bonded (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41) and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Tables 10 to 966 of Japanese Patent Application No. 2017-016290. Among the compounds, in the compounds excluding the compounds shown in Tables 10 to 11 below, ^{groups corresponding to −OCO-R 102} and the like can be mentioned, and more preferably 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) carbonization. A carbonyloxy group to which a hydrogen group or an inductive group thereof is bonded (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is more preferably 2 to 12), and Tables 1 to 8 and 9 below (Tables 1 to 8 and Table 9 below). In the compounds shown in a), Table 9 (b) and Tables 10 to 11, ^{the groups corresponding to -OCO-R 102} and the like can be mentioned.
-COCO-R ¹⁰² includes methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl) hexyloxalyl group, heptyloxalyl group, octyloxalyl group and nonyl. Oxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p-tolyloxalyl group and the like, and groups represented by the above formulas and the like. A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), 1 to 1 carbon atoms). Oxalyl groups to which 10 alkylsulfamoyl groups (preferably groups derivatized with an octylsulfamoyl group) or the like are bonded and Tables 1 to 8, Table 9 (a), Table 9 (b) and Table 10 ~ Among the compounds shown in Table 11 and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290, the groups corresponding to ^{−COCO-R 102 are listed in the compounds excluding the compounds shown in Tables 10 to 11 below.} Be done.
-O-R ¹⁰² includes hydroxy groups; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy. Group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyl Oxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3, 5-Dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy Group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as an ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula, or an inducing group thereof (for example, carboxy). A group derived from a group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably an octyl sulfamoyl group), or the like is bonded. Among the oxy groups and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290, the following Examples of the compounds excluding the compounds shown in Tables 10 to 11 include ^{groups corresponding to −O-R 102} , more preferably a hydrocarbon group having 1 to 10 carbon atoms or an oxy group to which a derivatizing group thereof is bonded, and the following. In the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, ^{the groups corresponding to -OR 102} and the like can be mentioned.
-SO _2- R ¹⁰¹ includes methyl sulfonyl group, ethyl sulfonyl group, propyl sulfonyl group, butyl sulfonyl group, pentyl sulfonyl group, hexyl sulfonyl group, (2-ethyl) hexyl sulfonyl group, heptyl sulfonyl group, octyl sulfonyl group, Nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc., and the group represented by the above formula, etc. have 1 to 40 carbon atoms (1 to 40 carbon atoms). A hydrocarbon group having 1 to 20 carbon atoms or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms). (Preferably octylsulfamoyl group) or the like-derived sulfonyl group and compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11. and group corresponding to -SO ₂ -R ¹⁰¹ are exemplified in the compounds except the compounds shown in Table 10-11 below among the compounds shown in Table 10 to 966 of Japanese Patent Application No. 2017-016290, more preferably carbon In the sulfonyl groups to which the hydrocarbon groups of numbers 1 to 10 or their derivatizing groups are bonded, and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11 below. Examples include groups corresponding to _{−SO 2} −R ^101.
-SO ₂ N (R ¹⁰² ) ₂ is a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butyl sulfamoyl group, N-tert-butyl sulfamoyl group, N-pentyl sulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N-hexyl sulfamoyl group, N- (2-) Ethyl) Hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N- One carbon number of 1 to 40 (preferably 1 to 20) of one such as a dodecylsulfamoyl group, an N-icosylsulfamoyl group, an N-phenylsulfamoyl group, and a group represented by the above formula). Hydro group or derivatizing group thereof (for example, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octyl sulfamoyl group). The sulfamoyl group substituted with () or the like and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Table 10 to Table 11, and Japanese Patent Application No. 2017-016290. Among the compounds shown in Tables 10 to 966 of the above, the groups corresponding to _{−SO 2} N (R ¹⁰¹ ) _{2 in the compounds excluding the compounds shown in Tables 10 to 11 below;}
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-dipropylsulfamoyl Group, N, N-isopropylmethylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-diisobutylsulfamoyl group, N, N- Disec-butylsulfamoyl group, N, N-ditert-butylsulfamoyl group, N, N-butylmethylsulfamoyl group, N, N-dibutylsulfamoyl group, N, N-dipentylsulfa Moyl group, N, N-di (1-ethylpropyl) sulfamoyl group, N, N-dihexyl sulfamoyl group, N, N-di (2-ethyl) hexyl sulfamoyl group, N, N-diheptylsul Famoyl group, N, N-octylmethylsulfamoyl group, N, N-dioctylsulfamoyl group, N, N-dinonylsulfamoyl group, N, N-decylmethylsulfamoyl group, N, N- Undecylmethylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N, N-icosylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group, N, N-diphenylsulfamoyl Two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group and a group represented by the above formula or a derivatizing group thereof (for example, a carboxy group, a sulfo group, a nitro group, etc.) Sulfamoyl groups substituted with hydroxy groups, halogens (preferably chlorine atoms), groups derivatized with alkylsulfamoyl groups having 1 to 10 carbon atoms (preferably octylsulfamoyl groups), etc. and Tables 1 to 1 and Table. 8. Among the compounds shown in Table 9 (a), Table 9 (b) and Tables 10 to 11, and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290, the compounds shown in Tables 10 to 11 below. Examples of the compounds excluding the above include _{groups corresponding to −SO 2} N (R ¹⁰¹ ) ₂ , and more preferably one or two sulfamoyl groups substituted with a hydrocarbon group having 1 to 10 carbon atoms or an inductive group thereof. , And the groups corresponding to _{−SO 2} N (R ¹⁰¹ ) ₂ in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11 below.
-CON (R ¹⁰² ) ₂ is a carbamoyl group;
N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarbamoyl group, N-tert-butylcarbamoyl group. Group, N-pentylcarbamoyl group, N- (1-ethylpropyl) carbamoyl group, N-hexylcarbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N- One of nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamoyl group, N-phenylcarbamoyl group, etc., and a group represented by the above formula. A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), and 1 to 10 carbon atoms). Carbamoyl groups substituted with an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) or the like and Tables 1 to 8, Tables 9 (a), 9 (b) and Table 10 ~ The groups corresponding to ^{−CON (R 102} ) ₂ in the compounds shown in Table 11 and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290 excluding the compounds shown in Tables 10 to 11 below, etc. ;
N, N-dimethylcarbamoyl group, N, N-ethylmethylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-propylmethylcarbamoyl group, N, N-dipropylcarbamoyl group, N, N-isopropylmethylcarbamoyl Group, N, N-diisopropylcarbamoyl group, N, N-tert-butylmethylcarbamoyl group, N, N-diisobutylcarbamoyl group, N, N-disec-butylcarbamoyl group, N, N-ditert-butylcarbamoyl group. , N, N-butylmethylcarbamoyl group, N, N-dibutylcarbamoyl group, N, N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N, N-di (1-ethylpropyl) carbamoyl group, N , N-dihexylcarbamoyl group, N, N-di (2-ethyl) hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N, N-octylmethylcarbamoyl group, N, N-dioctylcarbamoyl group, N, N -Dinonylcarbamoyl group, N, N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N, N-dodecylmethylcarbamoyl group, N, N-icosylmethylcarbamoyl group, N, N-phenylmethyl Two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a carbamoyl group, an N, N-diphenylcarbamoyl group, and a group represented by the above formula or an inducing group thereof (for example, 1 to 20 carbon atoms). Substituted with a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), or the like). Of the carbamoyl groups and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290. Examples of the compounds other than the compounds shown in Tables 10 to 11 below include ^{groups corresponding to −CON (R 102} ) ₂ , and more preferably one or two hydrocarbon groups having 1 to 10 carbon atoms or derivatization thereof. A carbamoyl group substituted with a group and a group corresponding to ^{-CON (R 102} ) ₂ in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Table 10 to Table 11 below. And so on.
-N (R ¹⁰² ) ₂ is an amino group;
N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino Group, N-pentylamino group, N-hexylamino group, N- (2-ethyl) hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-un A decylamino group, an N-dodecylamino group, an N-icosylamino group, an N-phenylamino group, etc., and a group represented by the above formula, which have 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms). A hydrocarbon group or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)). Amino groups substituted with (groups derived from such as) and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Japanese Patent Application No. 2017-016290. Among the compounds shown in Tables 10 to 966, the groups corresponding to ^{−N (R 102} ) ₂ in the compounds excluding the compounds shown in Tables 10 to 11 below;
N, N-dimethylamino group, N, N-ethylmethylamino group, N, N-diethylamino group, N, N-propylmethylamino group, N, N-dipropylamino group, N, N-isopropylmethylamino group , N, N-diisopropylamino group, N, N-tert-butylmethylamino group, N, N-diisobutylamino group, N, N-disec-butylamino group, N, N-ditert-butylamino group, N, N-butylmethylamino group, N, N-dibutylamino group, N, N-dipentylamino group, N, N-di (1-ethylpropyl) amino group, N, N-dihexylamino group, N, N -Di (2-ethyl) hexylamino group, N, N-diheptylamino group, N, N-dioctylamino group, N, N-dinonylamino group, N, N-decylmethylamino group, N, N-undecyl Methylamino group, N, N-dodecylmethylamino group, N, N-icosylmethylamino group, N, N-phenylmethylamino group, N, N-diphenylamino group, etc., and groups represented by the above formulas. Two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or derivatizing groups thereof (for example, carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), carbon Amino groups substituted with an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) having the number 1 to 10 and Tables 1 to 8, Table 9 (a) and Table 9 (b). ) and compounds shown in tables 10 11, and -N (R ¹⁰² in the compound except the compounds shown in Table 10-11 below among the compounds shown in Table 10 to 966 of Japanese Patent Application No. 2017-016290) to ₂ Applicable groups, etc .; more preferably, amino groups substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or derivatizing groups thereof, and Tables 1 to 8 and 9 (Tables 9 below). In the compounds shown in a), Table 9 (b) and Tables 10 to 11, the groups corresponding to ^{−N (R 102} ) _{2 can be mentioned.}
-NHCO-R ¹⁰² includes formylamino group; acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanolamino group, pentanoylamino group, hexanoylamino group, (2-ethyl). ) Hexanoylamino group, Heptanoylamino group, Octanoylamino group, Nonanoylamino group, Decanoylamino group, Undecanoylamino group, Dodecanoylamino group, Henikosanoylamino group, Benzoylamino group, etc., and A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula or an inducing group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, or a halogen (preferably). Is a chlorine atom), a carbonylamino group (a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) bonded to the carbonylamino group (when the carbonylamino group is an acylamino group). , 1 to 40 carbon atoms) and the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Tables 10 to 966 of Japanese Patent Application No. 2017-016290. ^{Among the compounds shown in the above, the compounds corresponding to −NHCOR 102} are mentioned in the compounds other than the compounds shown in Tables 10 to 11 below, and more preferably, a hydrocarbon group having 1 to 10 carbon atoms or a derivatizing group thereof is bonded. (When the carbonylamino group is an alkanoylamino group, the number of carbon atoms is more preferably 1 to 10), and Tables 1 to 8, Table 9 (a) and Table 9 (b) below. In addition, in the compounds shown in Tables 10 to 11, ^{the groups corresponding to -NHCOR 102} and the like can be mentioned.
-NHCON (R ¹⁰² ) ₂ includes the groups listed above, the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Japanese Patent Application No. 2017-. Among the compounds shown in Tables 10 to 966 of 016290, the compounds ^{corresponding to −NHCON (R 102} ) ₂ are mentioned in the compounds excluding the compounds shown in Tables 10 to 11 below.
-NHCOOR ¹⁰² includes the groups listed above, the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Table 10 of Japanese Patent Application No. 2017-016290. Among the compounds shown in ~ 966, the groups corresponding to ^{−NHCOOR 102} are mentioned in the compounds excluding the compounds shown in Tables 10 to 11 below.
-OCON (R ¹⁰² ) ₂ includes the groups listed above, the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Japanese Patent Application No. 2017-. Among the compounds shown in Tables 10 to 966 of 016290, the compounds ^{corresponding to −OCON (R 102} ) ₂ are mentioned in the compounds excluding the compounds shown in Tables 10 to 11 below.
As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like are preferable.
Examples of _{M of −SO 3} M and −CO ₂ M include hydrogen atom; alkali metal atom such as lithium atom, sodium atom and potassium atom, and preferably hydrogen atom, sodium atom and potassium atom.

-CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON Substituents (first substituents) contained in (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCON (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰² ) _2. May be one or more, and the two or more substituents may be independent of each other and may be the same or different.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group contained in a part thereof. The second substituent can be selected from the same groups as the first substituent.

The ^{rings formed by R 2} and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ are fused with the benzene ring of the isoindoline skeleton of formula (I). The fused ring structure of the ring formed by R ² and R ³ , R ³ and R ⁴ , or R ⁴ and R ⁵ and the benzene ring includes inden, naphthalene, biphenylene, indacene, anthracene, fluorene, phenalene, and phenanthrene. Hydrocarbon-based condensed ring structures such as anthracene, fluoranthene, acephenanthrene, aceanthrene, triphenylene, pyrene, chrysen, N-methylphthalimide, N- (1-phenylethyl) phthalimide and tetracene and their partial reductions (eg,). , 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Examples thereof include nitrogen-containing condensed heterocycles such as perimidine, phenanthrene and phenazine and their partial reductions; oxygen-containing condensed heterocycles such as 3-hydrobenzofuran-2-one and their partial reductions.

If R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ form a ring, the ring may have a substituent. Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} The preferred substituent is the same as the preferred substituent that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Things can be mentioned.

When R ³ and R ⁴ form a ring, R ² and R ⁵ are independent of each other, preferably a hydrogen atom, amino group or hydroxy group.
When R ² and R ³ form a ring, preferably R ⁴ and R ⁵ do not form a ring, and more preferably R ⁴ and R ⁵ are hydrogen atoms.
In the case where R ⁴ and R ⁵ form a ring, R ² and R ³ preferably may not form a ring, and more preferably R ² and R ³ are hydrogen atoms.

R ¹² and ring and R ¹³ form is coupled with isoindoline skeleton of exomethylene (C = CH ₂₎ of formula (I), R ¹² and ring the exomethylene which R ¹³ to form (C As a structure containing = CH ₂ ), for example, a structure in which a carbonyl group, an exomethylene, and a carbonyl group are arranged in this order as in groups A and B below can be exemplified. ** represents a bond with the isoindoline skeleton.

[Group A]

[Group B]

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -COCO-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.

R ¹⁰⁴ and R ¹⁰⁵ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N ( R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, with substituent It is preferable to represent a hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.

Represented by R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ , -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -COCO-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² ,- OCON (R ¹⁰² ) ₂ , halogen atom, -SO ₃ M and -CO ₂ M, which may have a substituent may have a hydrocarbon group having 1 to 40 carbon atoms or a heterocycle which may have a substituent. The groups are represented by R ^{1 to} R ⁵ , R ¹² and R ¹³ , -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -COCO-R ¹⁰² , -SO. _2- R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, -SO ₃ M, -CO ₂ M, may have a substituent or may have a hydrocarbon group or a substituent having 1 to 40 carbon atoms. The same as the heterocyclic group can be mentioned.

Preferred examples of R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ include the same preferred ones in R ^{1 to} R ⁵ , R ¹² and R ¹³ .

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ are independent of each other as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a (2-ethyl) hexyl group. , A hydrocarbon group having 1 to 10 carbon atoms such as a heptyl group, an octyl group, a nonyl group, a cyclohexyl group and a phenyl group, or a hydrogen atom is preferable.

In the groups exemplified in Group A and Group B, the hydrogen atom bonded to the ring structure may be substituted with a substituent.
Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
Among the substituents, preferred ones are preferred substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} The same thing can be mentioned.
It is preferable ^{that R 1} is a hydrogen atom and R ^{2 to} R ⁵ are hydrogen atoms or nitro groups independently of each other.

Examples of the group A and the group B include rings represented by the formulas (QQ1) to (QQ25) and the formulas (QQA1) to (QQA35) of Japanese Patent Application No. 2017-016290.

When R ¹² and R ¹³ do not form a ring, the compound (I) is a compound represented by the formula (Ia) (hereinafter, may be referred to as a compound (Ia)), the formula (II). (Hereinafter, sometimes referred to as compound (II)), compound represented by formula (II-a0) (hereinafter, may be referred to as compound (II-a0)), formula (II-). It is preferably a compound represented by a1) (hereinafter, may be referred to as a compound (II-a1)), and a compound represented by the formula (Ia) is more preferable.

[In the formula (Ia), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
L ² represents −CO − or −SO _2−.
R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. ]

A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by R ¹⁴ or a heterocyclic group which may have a substituent may be represented by ^{R 11} and R ^101. Examples thereof include the same hydrocarbon groups having 1 to 40 carbon atoms which may have a group or heterocyclic groups which may have a substituent.
Preferred R ¹⁴ includes the same preferred ones for R ¹¹ and R ¹⁰¹ .

In compound (Ia), R ¹¹ and R ¹⁴ are preferably the same group.
Further, ^{it is preferable that L 1} and L ² are the same group.
R ¹¹ and R ¹⁴ may have an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, and a substituent which are independent of each other. A naphthyl group, a tetrahydronaphthyl group which may have a substituent, a pyridinyl group which may have a substituent, a thienyl group which may have a substituent, and a frill which may have a substituent. It is preferably a pyridinyl group which may have a group or a substituent.
The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 8 carbon atoms.
The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the frill group and the alkyl group may have a substituent. These groups may have an alkyl group attached instead of the substituent.
Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
Preferred substituents include the same preferred substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Be done.
The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the frill group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl. The group, the frill group and the substituent of the pyridinyl group are carbons such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a (2-ethyl) hexyl group and an octyl group. Alkyl group of number 1 to 10; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; trifluoromethyl group; oxycarbonyl group to which hydrocarbon group of carbon number 1 to 10 is bonded; nitro group; hydroxy group Sulfamoyl group; -SO ₃ M; -CO ₂ M is preferred.
The substituent of the alkyl group is preferably a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a hydroxy group; −SO ₃ M; −CO _{2 M.}
L ¹ is preferably −CO−.
L ² is preferably −CO−.
R ¹ is preferably a hydrogen atom.
R ^{2 to} R ⁵ are preferably hydrogen atoms, halogen atoms or nitro groups independently of each other. The halogen atom is preferably a fluorine atom, a chlorine atom and a bromine atom, and more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. It is preferable that R ³ or R ⁴ is a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. It is preferable that R ³ or R ⁴ is a nitro group.

[In formula (II), R ^{1 to} R ⁵ , R ^{11 to} R ^13, and wavy lines have the same meanings as described above. ]

R ¹¹ may have a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, and a substituent. It is preferably a pyridinyl group, a thienyl group which may have a substituent, a frill group which may have a substituent or an alkyl group which may have a substituent. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 8 carbon atoms.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the frill group and the alkyl group may have a substituent. These groups may have an alkyl group attached instead of the substituent.
Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
Preferred substituents include the same preferred substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Be done.
The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the frill group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl. The group, the frill group and the substituent of the pyridinyl group are carbons such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a (2-ethyl) hexyl group and an octyl group. Alkyl group of number 1 to 10; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; trifluoromethyl group; oxycarbonyl group to which hydrocarbon group of carbon number 1 to 10 is bonded; nitro group; hydroxy group Sulfamoyl group; -SO ₃ M; -CO ₂ M is preferred.
The substituent of the alkyl group is preferably a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a hydroxy group; −SO ₃ M; −CO _{2 M.}
R ¹ is preferably a hydrogen atom.
R ^{2 to} R ⁵ are preferably hydrogen atoms, halogen atoms or nitro groups independently of each other. The halogen atom is preferably a fluorine atom, a chlorine atom and a bromine atom, and more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. It is preferable that R ³ or R ⁴ is a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. It is preferable that R ³ or R ⁴ is a nitro group.
R ¹² is preferably -CO-R ¹⁰² or -SO _2- R ^101. R ¹² is more preferably −CO—R ^102.
R ¹³ is preferably a cyano group.
R ¹⁰¹ and R ¹⁰² have the same meanings as described above, respectively.

The compound (I) is preferably a compound represented by the formula (II-a0) (hereinafter, may be referred to as a compound (II-a0)).

[In the formula (II-a0), R ^{1 to} R ⁵ , R ^{12 to} R ¹³ and the wavy line have the same meanings as described above.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
However, if one of R ¹² and R ¹³ is a cyano group and the other of R ¹² and R ¹³ is a group represented by −SO _2- R ^{223 , then R 2 to} R ⁵ At least one of is -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N (R ^102). ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, Represents a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. If R ² and R ³ form a ring, then R ⁴ and R ⁵ do not form a ring.
R ²²² represents a hydrocarbon group having carbon atoms of 1 to 40 which may have a substituent.
R ²²³ is the same ^{as R 222.}
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.

As the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by ^{R 222} , the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by ^{R 11 may be used.} The same thing as the group can be mentioned.
Preferred hydrocarbon groups having 1 to 40 carbon atoms which may have a substituent represented by R ²²² are those having 1 to 40 carbon atoms which may have a substituent represented by ^{R 11.} The same as the preferred one of the hydrocarbon groups of.
^R222 may have a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent or a substituent. It is preferably an alkyl group. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 8 carbon atoms.
The phenyl group, the naphthyl group, the tetrahydronaphthyl group and the alkyl group may have a substituent. These groups may have an alkyl group attached instead of the substituent.
Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
The preferred substituent is the same as the preferred substituent that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Things can be mentioned.

The phenyl group, the naphthyl group, the alkyl group that may be bonded to the tetrahydronaphthyl group, or the substituent of the phenyl group, the naphthyl group, or the tetrahydronaphthyl group is a methyl group, an ethyl group, a propyl group, or an isopropyl. Alkyl groups having 1 to 10 carbon atoms such as groups, butyl groups, tert-butyl groups, hexyl groups, (2-ethyl) hexyl groups and octyl groups; halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms and iodine atoms; It is preferably a trifluoromethyl group; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms is bonded; a nitro group; a hydroxy group; a sulfamoyl group; -SO ₃ M; -CO ₂ M.
The substituent of the alkyl group is preferably a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a hydroxy group; −SO ₃ M; −CO _{2 M.}
R ¹ is preferably a hydrogen atom.
R ^{2 to} R ⁵ are preferably hydrogen atoms, halogen atoms or nitro groups independently of each other. The halogen atom is preferably a fluorine atom, a chlorine atom and a bromine atom, and more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. It is preferable that R ³ or R ⁴ is a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. It is preferable that R ³ or R ⁴ is a nitro group.
R ¹² is preferably -CO-R ¹⁰² or -SO _2- R ^101. R ¹² is more preferably _{−SO 2} −R ^101.
R ¹³ is preferably a cyano group.
R ¹⁰¹ and R ¹⁰² have the same meanings as described above, respectively.
The compound (I) is preferably a compound represented by the formula (II-a1) (hereinafter, may be referred to as a compound (II-a1)).

[In the formula (II-a1), R ^{1 to} R ⁵ , R ^{12 to} R ¹³ and the wavy line have the same meanings as described above.
R ¹¹¹ represents a heterocycle which may have a substituent. ]

^Examples of the heterocyclic group which may have a substituent represented by R 111 include the same heterocyclic group which may have a substituent represented by ^{R 11.}
Preferred examples of the heterocyclic group which may have a substituent represented by R ¹¹¹ include the same preferred ones of the heterocyclic group which may have a substituent represented by ^{R 11.} Be done.
R ¹¹¹ is preferably a pyridinyl group, a thienyl group and a frill group which may have a substituent.
The pyridinyl group, the thienyl group and the frill group may have a substituent. These groups may have an alkyl group attached instead of the substituent.
Examples of the substituent include the same substituents that the hydrocarbon group represented by ^{R 11 may have.}
Preferred examples of the substituent include the same preferred substituents that the hydrocarbon group represented by ^{R 11 may have.}
The thienyl group, the frill group and the alkyl group which may be bonded to the pyridinyl group, or the thienyl group, the frill group and the substituent of the pyridinyl group are methyl group, ethyl group, propyl group, isopropyl group, and the like. Alkyl groups having 1 to 10 carbon atoms such as butyl group, tert-butyl group, hexyl group, (2-ethyl) hexyl group and octyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Trifluoromethyl group; oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms is bonded; nitro group; hydroxy group; sulfamoyl group;
-SO ₃ M; preferably _{-CO 2 M.}
R ¹² is preferably -CO-R ¹⁰² or -SO _2- R ^101. R ¹² is more preferably _{−SO 2} −R ^101. R ¹⁰¹ and R ¹⁰² have the same meanings as described above, respectively.
R ¹³ is preferably a cyano group.
R ¹ is preferably a hydrogen atom.
R ^{2 to} R ⁵ are preferably hydrogen atoms, halogen atoms or nitro groups independently of each other. The halogen atom is preferably a fluorine atom, a chlorine atom and a bromine atom, and more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. It is preferable that R ³ or R ⁴ is a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. It is preferable that R ³ or R ⁴ is a nitro group.

When R ¹² and R ¹³ form a ring, the compound (I) is preferably a compound represented by the formula (I-b) (hereinafter, may be referred to as a compound (I-b)). ..

[In the formula (I-b), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ²⁰ and R ³⁰ combine to form a ring Q.
The ring Q may have a substituent and has 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocycle. A single ring having 5 to 7 ring members or a condensed ring obtained by condensing the single ring, which is selected from a hydrocarbon ring and a heterocycle, may be bonded to the ring Q. ]

The number of ring members is preferably 5 to 6 rings.
It is preferable that these monocyclic or condensed rings are combined with the ring Q at two points to form a condensed ring.
Examples of the ring Q and the ring to which a monocyclic ring or a condensed ring is bonded include the same rings as those in the group A and the group B, and are preferably rings represented by the formulas (QQ1) to (QQ25).
Of these, the ring is preferably represented by the formula (Q1), the formula (Q4), the formula (Q7), the formula (Q8), the formula (Q18) (preferably the formula (QQ25) among the formulas (Q18)). , More preferably the ring represented by the formula (Q8), the formula (Q18) (preferably the formula (QQ25) among the formulas (Q18)).

Ring Q, and two or more monocycles or monocycles that may have 5 to 7 substituents, selected from hydrocarbon rings and heterocycles that may be condensed into ring Q. The fused ring may have a substituent. Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
The preferred substituent is the same as the preferred substituent that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Things can be mentioned.

The compound (Ib) is more preferably a compound represented by the formula (Ic) (hereinafter, may be referred to as a compound (Ic)).

[In the formula (I-c), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ⁶ and R ⁷ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ^101. , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON ( R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group or a substituent having 1 to 40 carbon atoms which may have a substituent. Represents a good heterocycle.
R ¹⁰¹ , R ¹⁰² and M have the same meanings as described above. ]

R ⁶ and R ⁷ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N ( R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , Halogen atom, Cyano group, Nitro group, -SO ₃ M, -CO ₂ M, Substituent It is preferable to represent a hydrocarbon group having 1 to 40 carbon atoms or a heterocycle which may have a substituent.

Represented by R ⁶ and R ⁷ , -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -COCO-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , Halogen atom, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and a heterocyclic group which may have a substituent are R ¹ to Represented by R ⁵ , R ¹² and R ¹³ , -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -COCO-R ¹⁰² , -SO _2- R ¹⁰¹ ,- SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON (R ¹⁰²⁾ ) ₂ , Halogen atom, -SO ₃ M, -CO ₂ M, the same as the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and the heterocyclic group which may have a substituent. Can be mentioned.

Preferred R ⁶ and R ⁷ include the same preferred ones in R ^{1 to} R ⁵ , R ¹² and R ¹³ .

In the compound (I-b) or the compound (I-c), R ¹¹ has a phenyl group which may have a substituent, a naphthyl group which may have a substituent, and a substituent. It may have a tetrahydronaphthyl group, a pyridinyl group which may have a substituent, a thienyl group which may have a substituent, a frill group which may have a substituent or a substituent. It is preferably an alkyl group having 1 to 40 carbon atoms.
When R ¹¹ is an alkyl group which may have a substituent, the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and has 1 to 10 carbon atoms. It is more preferably 1 to 8.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the frill group and the alkyl group may have a substituent. These groups may have an alkyl group attached instead of the substituent.
Examples of the substituent include the same substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.}
Preferred substituents include the same preferred substituents that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Be done.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the frill group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl. The group, the frill group and the substituent of the pyridinyl group are carbons such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a (2-ethyl) hexyl group and an octyl group. Alkyl group of number 1 to 10; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; trifluoromethyl group; oxycarbonyl group to which hydrocarbon group of carbon number 1 to 10 is bonded; nitro group; hydroxy group Sulfamoyl group; -SO ₃ M; -CO ₂ M is preferred.
The substituent of the alkyl group is preferably a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a hydroxy group; −SO ₃ M; −CO _{2 M.}

R ¹ is preferably a hydrogen atom.
L ¹ is preferably −CO−.
R ^{2 to} R ⁵ are preferably hydrogen atoms, halogen atoms or nitro groups independently of each other. The halogen atom is preferably a fluorine atom, a chlorine atom and a bromine atom, and more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. It is preferable that R ³ or R ⁴ is a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. It is preferable that R ³ or R ⁴ is a nitro group.

R ⁶ and R ⁷ are ^{preferably the same as the preferred ones of R 1 to} R ⁵ , R ¹² and R ¹³ independently of each other, and independently of each other, a methyl group, an ethyl group, a propyl group and an isopropyl group. A hydrocarbon group or hydrogen atom having 1 to 10 carbon atoms such as a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group and a phenyl group. Is more preferable.

As a specific example of the compound (I), for example, in the formula (I-aa), the compounds having the substituents shown in Tables 1 to 4 and 9 (a) (Compounds 1 to 360 and Compounds 725 to 745) are used. Can be mentioned.
B ¹ B ² represents any partial structure represented by the equations (BB 1) to (BB 60).
As B ¹ B ² , the formula (BB 1), the formula (BB 6) or the formula (BB 19) is preferable.
R ¹¹ and R ¹⁴ represent any of the partial structures represented by the formulas (HH1) to (HH89).

Specific examples of the compound (I) include, for example, compounds having a substituent shown in Tables 5 to 8 and Table 9 (b) in the formula (I-bb) (Compounds 361 to 724 and Compounds 746 to 746). 759) can be mentioned.
B ¹ B ² represents any partial structure represented by the equations (BB 1) to (BB 60).
As B ¹ B ² , the formula (BB 1), the formula (BB 6) or the formula (BB 19) is preferable.
QQ represents any partial structure represented by the equations (QQ1) to (QQ25). As QQ, the formula (QQ25) is preferable.
R ¹¹ represents any of the partial structures represented by the equations (HH1) to (HH89).

Other specific examples of the compound (I) include, for example, a compound of the formula (I-aa) having a substituent shown in Table 10 and a compound of the formula (I-bb) having a substituent shown in Table 11. Be done. Further, the compound (I) may be a compound excluding the compound having a substituent shown in the following Tables 10 to 11 among the compounds shown in Tables 10 to 966 of Japanese Patent Application No. 2017-016290.
B ¹ B ² represents any partial structure represented by the formula (BB1) to the formula (BB60), the formula (BBD1), the formula (BBI1), the formula (BBJ2), and the formula (BBO10).
R ¹¹ and R ¹⁴ are the formulas (HH1) to (HH89), formulas (HHJ5), formulas (HHJ6), formulas (HHJ7), formulas (HHJ10), formulas (HHJ14), formulas (HHJ15), and formulas (HHk5). ), The formula (HHk6), or the partial structure represented by the formula (HHk7).
QQ represents any partial structure represented by the equations (QQ1) to (QQ25).

Each symbol in Tables 1 to 9 (b) and Tables 10 to 11 represents the following partial structure.
In the partial structure, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. In addition, *, B ¹ , B ² and ** each represent a bond.
In each partial structure, even if the substituent to be substituted for the ring structure is only exemplified at the ortho-position, para-position, or meta-position, the following examples include the ortho-position, para-position, and meta. Three embodiments are included in which each position is replaced.

Compounds 1 to 12, Compounds 100 to 360, Compounds 448 to 759, Compounds 01-10, Compounds 01-124, Compounds 01-138, Compounds 01-151, Compounds 01-24, Compounds 01-364, Compounds 01. -37, compound 01-378, compound 01-391, compound 21-107, compound 21-108, compound 21-117, compound 21-118, compound 21-119, compound 21-13, compound 21-135, compound 21 -14, Compound 21-144, Compound 21-15, Compound 21-167, Compound 21-168, Compound 21-169, Compound 21-185, Compound 21-219, Compound 21-292, Compound 21-293, Compound 21 -294, compound 21-30, compound 21-31, compound 21-32, compound 21-34, compound 21-37, compound 21-38, compound 21-39, compound 21-4, compound 21-40, compound 21 -43, compound 21-46, compound 21-48, compound 21-5, compound 21-53, compound 21-55, compound 21-87, compound 21-88, compound 21-89, compound 22-10, compound 22 -1411, compound 22-1414, compound 22-1417, compound 22-1439, compound 22-1440, compound 22-3565, compound 22-3566, compound 22-3569, compound 22-3570, compound 22-4, compound 22 −4941, Compound 22-5, Compound 22-6, Compound 22-7, Compound 22-8, Compound 22-9, Compound 51-28, Compound 52-2436, Compound 31-107, Compound 31-31, Compound 31 -32, compound 31-34, compound 31-37, compound 31-38, compound 31-39, compound 31-40, compound 31-43, compound 31-46, compound 31-49, compound 31-5, compound 31 -54, Compound 32-1411, Compound 32-1414, Compound 32-1417, Compound 41-842, Compound 41-843, Compound 41-845, Compound 71-25, Compound 71-30, Compound 72-12 are preferable.
Compounds 1 to 12, compounds 100 to 273, compounds 448 to 637 and compounds 725 to 759 are more preferred.
Compound 1-Compound 12, Compound 100-Compound 168, Compound 186-Compound 255, Compound 273, Compound 448-Compound 532, Compound 550-Compound 619, Compound 637, Compound 725-Compound 726, Compound 732-Compound 733, Compound 739 -Compound 740, Compound 746-Compound 747 and Compound 753-Compound 754 are more preferred.
Compound 100-Compound 168, Compound 186-Compound 255, Compound 273, Compound 464-Compound 532, Compound 550-Compound 619, Compound 637, Compound 732-Compound 733, Compound 739-Compound 740, Compound 746-Compound 747 and Compound 753 ~ Compound 754 is particularly preferred.

Specific examples of the compound (I) include the compounds represented by Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, and Tables 10 to 966 of Japanese Patent Application No. 2017-016290. Among the compounds shown in the above, compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded to the compounds excluding the compounds having the substituents shown in Tables 10 to 11 above can also be mentioned. For example, a compound in which 1 to 3 sulfo groups are bonded to compound 102 in Table 2 represents the following structure. However, in the formula, − (SO ₃ H) means that any hydrogen atom of compound 102 is substituted.

Compounds 1 to 12, Compounds 100 to 360, Compounds 448 to 759, Compounds 01-10, Compounds 01-124, Compounds 01-138, Compounds 01-151, Compounds 01-24, Compounds 01-364, Compounds 01. -37, compound 01-378, compound 01-391, compound 21-107, compound 21-108, compound 21-117, compound 21-118, compound 21-119, compound 21-13, compound 21-135, compound 21 -14, Compound 21-144, Compound 21-15, Compound 21-167, Compound 21-168, Compound 21-169, Compound 21-185, Compound 21-219, Compound 21-292, Compound 21-293, Compound 21 -294, compound 21-30, compound 21-31, compound 21-32, compound 21-34, compound 21-37, compound 21-38, compound 21-39, compound 21-4, compound 21-40, compound 21 -43, compound 21-46, compound 21-48, compound 21-5, compound 21-53, compound 21-55, compound 21-87, compound 21-88, compound 21-89, compound 22-10, compound 22 -1411, compound 22-1414, compound 22-1417, compound 22-1439, compound 22-1440, compound 22-3565, compound 22-3566, compound 22-3569, compound 22-3570, compound 22-4, compound 22 −4941, Compound 22-5, Compound 22-6, Compound 22-7, Compound 22-8, Compound 22-9, Compound 51-28, Compound 52-2436, Compound 31-107, Compound 31-31, Compound 31 -32, compound 31-34, compound 31-37, compound 31-38, compound 31-39, compound 31-40, compound 31-43, compound 31-46, compound 31-49, compound 31-5, compound 31 −54, compound 32-1411, compound 32-1414, compound 32-1417, compound 41-842, compound 41-843, compound 41-845, compound 71-25, compound 71-30, compound 72-12, 1 _{Compounds to which up to 3} -SO 3 M or -CO ₂ M are bound are preferred.
Compounds 1 to 12, compounds 100 to 273, compounds 448 to 637 and compounds 725 to 759 are more preferred.
Compound 1-Compound 12, Compound 100-Compound 168, Compound 186-Compound 255, Compound 273, Compound 448-Compound 532, Compound 550-Compound 619, Compound 637, Compound 725-Compound 726, Compound 732-Compound 733, Compound 739 _{-A compound in which 1 to 3 -SO 3} M or -CO ₂ M is bound to Compound 740, Compound 746 to Compound 747 and Compound 753 to Compound 754 is more preferable.
Compound 100-Compound 168, Compound 186-Compound 255, Compound 273, Compound 464-Compound 532, Compound 550-Compound 619, Compound 637, Compound 732-Compound 733, Compound 739-Compound 740, Compound 746-Compound 747 and Compound 753 -A compound in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded to compound 754 is particularly preferable.

As the compound (I), in the formula (I), L ¹ is −CO− or −SO ₂₋ , preferably −CO−, and R ¹ is a hydrogen atom or −SO ₃ M, and R ² ~ R ⁵ are each independently a hydrogen atom, a nitro group, -SO ₃ M, or a halogen atom, and R ¹¹ is -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -SO ₃ M, -CO. Fragrance of 6 to 10 carbon atoms which may have a substituent selected from the group consisting of ₂ M, -O-R ¹⁰² , -SO ₂ N (R ¹⁰² ) _{2, a halogen atom, a cyano group and a nitro group.} Group hydrocarbon groups, one of R ¹² and R ¹³ is a cyano group, and the other of R ¹² and R ¹³ is -CO-R ¹¹ or -SO _2- R ¹¹ , preferably. -CO-R ¹¹ , R ¹⁰¹ and R ¹⁰² are hydrogen atoms or aliphatic hydrocarbon groups having 1 to 8 carbon atoms, respectively, and M is preferably a compound which is a hydrogen atom or an alkali metal atom.
L ¹ is -CO- or -SO _2- , preferably -CO-, R ¹ is a hydrogen atom or -SO ₃ M, and R ^{2 to} R ⁵ are independent hydrogen atoms, respectively. It is a nitro group, -SO ₃ M, or a halogen atom, and R ¹¹ is -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -SO ₃ M, -CO ₂ M, -O-R ¹⁰² , -SO ₂ N. (R ¹⁰² ) _{2. A} phenyl group which may have a substituent selected from the group consisting of a halogen atom, a cyano group and a nitro group, and one of R ¹² and R ¹³ is a cyano group. , R ¹² and R ¹³ are -CO-R ¹¹ or -SO _2- R ¹¹ , preferably -CO-R ¹¹ , and R ¹⁰¹ and R ¹⁰² are hydrogen atoms or carbons, respectively. It is an alkyl group having the number 1 to 8, and M is more preferably a compound which is a hydrogen atom or an alkali metal atom.
Preferred compounds (I), in addition to the above compounds, a compound represented by the formula (I-c), L ¹ is, -CO- or -SO ₂ -, preferably -CO-, R ¹ is a hydrogen atom or -SO ₃ M, R ^{2 to} R ⁵ are independently hydrogen atoms, nitro groups, -SO ₃ M, or halogen atoms, and R ^{6 to} R ⁷ are respectively. , Independently, a hydrogen atom, -SO ₃ M, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group having 3 to 8 carbon atoms, and R ¹¹ is -COO-R ¹⁰¹ , -OCO-R. ^It has a substituent selected from the group consisting of 102, -SO ₃ M, -CO ₂ M, -O-R ¹⁰² , -SO ₂ N (R ¹⁰² ) ₂ , halogen atom, cyano group and nitro group. It is also a good aromatic hydrocarbon group having 6 to 10 carbon atoms, R ¹⁰¹ and R ¹⁰² are hydrogen atoms or aliphatic hydrocarbon groups having 1 to 8 carbon atoms, respectively, and M is a hydrogen atom or an alkali. Compounds that are metal atoms can also be mentioned.

As the compound (I), when R ¹ is a hydrogen atom, a compound represented by the formula (pt 1) (hereinafter, may be referred to as a phthalonitrile compound) is represented by a compound represented by the formula (pt 2) (hereinafter, referred to as an alkoxide compound). It can be produced by further reacting the compound represented by the formula (pt3) with the compound represented by the formula (pt4) in the presence of an acid. When R ¹ is other than a hydrogen atom, compound (I) can be produced by further reacting with a compound represented by the formula (pt 5).

Wherein (pt1) ~ formula (pt5) and Formula ^{(I), L 1, R} 1 ~R 5 and R ¹¹ to R ¹³ represent the same meanings as the above.
R ⁷⁷⁷ represents an alkyl group having 1 to 20 carbon atoms.
M ¹ represents an alkali metal atom.
LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. ]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ⁷⁷⁷ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, which are preferable. Is an alkyl group having 1 to 6 carbon atoms.
Examples ^{of the alkali metal atom represented by M 1} include a lithium atom, a sodium atom and a potassium atom.

The amount of the alkoxide compound used is usually 0.1 to 10 mol, preferably 0.2 to 5 mol, more preferably 0.3 to 3 mol, based on 1 mol of the phthalonitrile compound. More preferably, it is 0.4 to 2 mol.

The amount of the compound (pt3) used is usually 1 to 10 mol, preferably 1 to 5 mol, more preferably 1 to 3 mol, still more preferably 1 mol, relative to 1 mol of the phthalonitrile compound. ~ 2 mol.
The amount of the compound (pt4) used is usually 1 to 10 mol, preferably 1 to 5 mol, more preferably 1 to 3 mol, still more preferably 1 mol, relative to 1 mol of the phthalonitrile compound. ~ 2 mol.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; Examples include carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartrate acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and Examples include carboxylic acids, more preferably acetic acids.
The amount of the acid used is usually 1 to 20 mol, preferably 1 to 10 mol, more preferably 1 to 8 mol, still more preferably 1 to 6 mol, relative to 1 mol of the phthalonitrile compound. be.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound (pt3) and the compound (pt4) is usually carried out in the presence of a solvent.
As the solvent, water; a nitrile solvent such as acetonitrile; an alcohol solvent such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; an ether solvent such as tetrahydrofuran; a ketone solvent such as acetone; acetic acid. Ester solvents such as ethyl; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amides such as N, N-dimethylformaldehyde and N-methylpyrrolidone. Solvents; examples include sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N, N-dimethylformaldehyde. , N-Methylpyrrolidone and dimethylsulfoxide, more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, methylene chloride, chloroform, N, N. -Dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are mentioned, and water, acetonitrile, methanol, ethanol and 2-propanol are particularly preferable.
The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the phthalonitrile compound.

The reaction temperature is usually 0 to 200 ° C, preferably 0 to 100 ° C, more preferably 0 to 70 ° C, still more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

The amount of the compound (pt5) to be used is usually 1 to 10 mol, preferably 1 to 5 mol, and more preferably 1 to 3 mol with ^{respect to 1 mol of the compound (I) in which R 1 is a hydrogen atom.} It is more preferably 1 to 2 mol.

Further, when the compound (pt5) is reacted, it is preferable that a base coexists. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide, and butyl lithium. , Tert-Organic metal compounds such as butyllithium and phenyllithium; and inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.

The amount of the base used is usually 1 to 10 mol, preferably 1 to 5 mol, more preferably 1 to 3 mol, and further, with respect to 1 mol of the compound (I) in which ^{R 1 is a hydrogen atom.} It is preferably 1 to 2 mol.

The reaction of compound (pt5) is usually carried out in the presence of a solvent. The solvent can be selected from the same range as described above.
The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound (I) in which ^{R 1 is not a hydrogen atom.} The reaction temperature of the compound (pt5) is usually −90 to 200 ° C., preferably −80 to 100 ° C., and more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

If compound (I) _{does not have a sulfo group or -SO 3} M ² , compound (I) can be reacted with a sulphonizing agent such as fuming sulfuric acid or chlorosulfuric acid to cause a sulfo group or -SO ₃ M ^2. Can be introduced.
M ² represents an alkali metal atom.
Examples ^{of the alkali metal atom represented by M 2} include a lithium atom, a sodium atom and a potassium atom.

_{The amount of SO 3} used in fuming sulfuric acid is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, still more preferably 5 to 30 mol, relative to 1 mol of compound (I). It is 5 to 25 mol.
The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 mol, preferably 10 to 100 mol, more preferably 10 to 75 mol, and further preferably 10 to 1 mol of compound (I). ~ 50 mol.

The amount of chlorosulfonic acid used is usually 1 to 500 mol, preferably 10 to 300 mol, more preferably 10 to 200 mol, still more preferably 10 to 150 mol, relative to 1 mol of compound (I). It is a mole.

The reaction temperature for sulfonation is usually -20 to 200 ° C, preferably -10 to 100 ° C, and more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

The method for extracting compound (I) from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after completion of the reaction, compound (I) can be taken out by filtering the reaction mixture. Further, after filtering, the obtained residue may be subjected to column chromatography or recrystallization. Further, after completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.

<Kinophthalone compound>
Examples of the quinophthalone compound contained in the pigment composition of the present invention include compounds represented by the formulas (K-1) to (K-17).

[R ^{k1 to} R ^k266 are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N. (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHSO _2- R ¹⁰² , hydrogen atom, cyano group, nitro group, -SO ₃ H,- _{CO 2 H, -SO 2 Cl,} -SO-R 102; -SO 3 H or -CO ₂ 1 monovalent to trivalent metal salt of H; alkyl ammonium salts of -SO ₃ H or -CO ₂ H; substituents Represents a phthalimidomethyl group which may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
Adjacent groups of R ^{k1 to} R ^k266 may be integrated to form a ring which may have a substituent.
R ¹⁰¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
When ^{there are a plurality of R 101} and R ¹⁰² , they may be the same or different. ]

^Represented by R ^{k1 to} R k266, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , as halogen atoms, represented by R ^{1 to} R ⁵ , R ¹² and R ¹³ , -CO-R ¹⁰² , -COO -R ¹⁰¹ , -OCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ ,- NHCO-R ¹⁰² , the same as the halogen atom, may be mentioned, and these groups may further have a substituent, and the substituents include N, N-dimethylamino group and N, N-diethylamino group. , Amino group, 4-methyl-1-piperazinyl group, 4-ethyl-1-piperazinyl group, 1-piperidinyl group, 1-piperidinylmethyloxy group, 4-morpholinyl group and the like.

_{-NHSO 2-} R ¹⁰² represented by R ^{k1 to} R ^k265 includes a sulfonylamino group; a methylsulfonylamino group, an ethylsulfonylamino group, a propylsulfonylamino group, a butylsulfonylamino group, a pentylsulfonylamino group, and a hexylsulfonylamino. Group, (2-ethyl) hexylsulfonylamino group, heptylsulfonylamino group, octylsulfonylamino group, nonylsulfonylamino group, decylsulfonylamino group, undecylsulfonylamino group, dodecylsulfonylamino group, icosylsulfonylamino group, phenyl Examples thereof include an amino group substituted with a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms such as a sulfonylamino group and a p-tolylsulfonylamino group is bonded, and these groups may further have a substituent. As the substituent, N, N-dimethylamino group, N, N-diethylamino group, amino group, 4-methyl-1-piperazinyl group, 4-ethyl-1-piperazinyl group, 1-piperidinyl group, 1- Examples thereof include a piperidinylmethyloxy group and a 4-morpholinyl group.

-SO-R ¹⁰² represented by R ^{k1 to} R ^k265 includes a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group, and a (2-ethyl) hexylsulfinyl group. A hydrocarbon group having 1 to 20 carbon atoms such as a heptylsulfinyl group, an octylsulfinyl group, a nonylsulfinyl group, a decylsulfinyl group, an undecylsulfinyl group, a dodecylsulfinyl group, an icosylsulfinyl group, a phenylsulfinyl group and a p-tolylsulfonyl group. Examples thereof include a sulfinyl group to which is bonded, and these groups may further have a substituent, and the substituent includes an N, N-dimethylamino group, an N, N-diethylamino group, an amino group, 4 Examples thereof include -methyl-1-piperazinyl group, 4-ethyl-1-piperazinyl group, 1-piperidinyl group, 1-piperidinylmethyloxy group, 4-morpholinyl group and the like.

The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by R ^{k1 to} R ^{k266 or the heterocyclic group which may have a substituent may be R 1 to} R ⁵ , R. ^{The same as} a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by 11, R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 or a heterocyclic group which may have a substituent.} Things can be mentioned.

The _{monovalent to trivalent metal salts of the -SO 3} H or -CO ₂ H groups represented by ^{R k1 to} R ^k266 include alkali metal salts such as sodium salts and potassium salts; alkalis such as magnesium salts and calcium salts. Earth metal salts; iron salts; aluminum salts; etc.
The _{alkylammonium salts of −SO 3} H or −CO ₂ H include ammonium salts derived from monoalkylamines having 1 to 40 carbon atoms such as octylamine, laurylamine, and stearylamine; palmityltrimethylammonium and dilauryldimethyl. Examples thereof include quaternary alkylammonium salts such as ammonium and distealyldimethylammonium.
When the valence of the metal ion forming the metal salt of _{−SO 3} H or −CO ₂ H is divalent or higher, the ratio of the quinophthalone compound having _{−SO 3} ⁻ or −CO ₂ ^{− to the metal ion is electrical.} Adjusted according to the valence to maintain neutrality.

As a substituent in the phthalimide methyl group (C ₆ H ₄ (CO) ₂ N−CH ₂ −) which may have a substituent,
Halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom;
Linear group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n-hexyl group, n-octyl group, stearyl group, 2-ethylhexyl group and the like. Alkyl group with 1 to 20 carbon atoms in the form of a branched or branched; trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3 − An alkyl group having 1 to 20 carbon atoms in which a part or all of a hydrogen atom such as a tetrafluoropropyl group is substituted with a halogen atom; a 2-ethoxyethyl group, a 2-butoxyethyl group, a 2-nitropropyl group, etc. An alkyl group having 1 to 20 carbon atoms having a substituent;
Phenyl group, naphthyl group, anthranyl group, p-tolyl group, p-tert-butylphenyl group, p-bromophenyl group, p-nitrophenyl group, p-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl Group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 6-methyl-2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group , 2-Aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent such as an aminoanthraquinonyl group;
Alkyl groups having 1 to 20 carbon atoms such as benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group and 6 carbon atoms. A group combined with ~ 20 aromatic hydrocarbon groups;
Methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutyloxy group, tert-butyloxy group, neopentyloxy group, 2,3-dimethyl-3-pentyloxy group, n-hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group, trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group , 2,2-Ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, benzyloxy group, etc. An oxy group having 1 to 20 carbon atoms bonded to one side;
And so on.

Adjacent groups among the groups represented by R ^{k1 to} R ^k266 may be integrated to form a ring which may have a substituent. Examples of the ring include a saturated aliphatic hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring and an aromatic heterocycle, and an aromatic hydrocarbon ring and an aromatic heterocycle are preferable. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and the like, and examples of the aromatic heterocycle include a pyridine ring, a pyrazine ring, a pyrrole ring, a quinoline ring, a quinoxalin ring, and a furan ring. , Benzofuran ring, thiophene ring, benzothiophene ring, oxazole ring, thiazole ring, imidazole ring, pyrazole ring, indole ring, carbazole ring and the like. Further, as the substituent which the ring may have, the hydrocarbon group represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may be contained.} The same as the substituent can be mentioned. The preferred substituent is the same as the preferred substituent that the hydrocarbon groups represented by ^{R 1 to} R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may have.} Things can be mentioned.

Among the groups represented by R ^{k1 to} R ^k266 , preferred groups are a halogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, ^{-OR 102} , and -SO ₃ H. , -CO ₂ H, -SO ₃ H or -CO ₂ H monovalent to trivalent metal salt, -SO ₃ H or -CO ₂ H alkylammonium salt, phthalimide methyl which may have a substituent. A group, −SO ₂ N (R ¹⁰² ) _2, is mentioned, and more preferable groups include a halogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and −OR ^102. A more preferred group is a halogen atom.

Examples of the quinophthalone compound contained in the pigment composition of the present invention include quinophthalone dyes and quinophthalone pigments.
C.I. I. Known quinophthalone yellow dyes such as Acid Yellow 3
C.I. described in the Color Index (published by The Society of Dyers and Colorists). I. Known quinophthalone yellow pigments such as Pigment Yellow 138,
Equations (K-1-1) to Equations (K-1-2),
Equation (K-2-1) to Equation (K-2-68),
Equations (K-3-1) to Equations (K-3-23),
Formulas (K-4-1) to formulas (K-4-6), formulas (K-5-1) to formulas (K-5-6),
Equations (K-6-1) to Equations (K-6-50),
Equations (K-7-1) to Equations (K-7-4),
Equations (K-8-1) to Equations (K-8-2),
Equations (K-9-1) to Equations (K-9-2),
Equations (K-10-1) to Equations (K-10-6),
Equations (K-11-1) to Equations (K-11-2),
Equations (K-12-1) to Equations (K-12-2),
Equations (K-13-1) to Equations (K-13-2),
Equations (K-14-1) to Equations (K-14-6),
Equations (K-15-1) to Equations (K-15-2),
Formulas (K-16-1) to formulas (K-16-2) or formulas (K-17-1) to formulas (K-17-2),
The compound represented by is preferable.
C. I. Pigment Yellow 138,
Equations (K-1-1) to Equations (K-1-2),
Equation (K-2-1) to Equation (K-2-68),
Equations (K-3-1) to Equations (K-3-23),
Equation (K-4-1),
Equations (K-6-1) to Equations (K-6-50),
Equations (K-7-1) to Equations (K-7-4),
Equation (K-10-1), Equation (K-12-1)
Alternatively, the compound represented by the formula (K-14-1) is more preferable.
C. I. Pigment Yellow 138 is even more preferred.
These quinophthalone compounds may be used alone or in combination of two or more.

The pigment composition of the present invention may contain a colorant other than the compound (I) and the quinophthalone compound (hereinafter, may be referred to as a colorant (A1-1)).

<Colorant (A1-1)>
The colorant (A1-1) may be a dye or a pigment.

As the dye, a known dye can be used, and examples thereof include dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). Further, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes and the like can be mentioned. These dyes may be used alone or in combination of two or more.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic green 1;
C. I. Bat green 1 etc.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). These can be used alone or in combination of two or more.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, Red pigments such as 268, 269, 273;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments;
C. I. Examples thereof include green pigments such as Pigment Green 7, 36, 58 and 59.

Other colorants (A1-1) include yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants"), green dyes and green pigments (hereinafter, these are collectively referred to as "yellow colorants"). (Sometimes referred to as a green colorant)) is preferred, yellow pigments and green pigments are more preferred, and green pigments are even more preferred.
Examples of the yellow dye include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.
Among the yellow pigments, metal-containing yellow pigments and isoindoline yellow pigments are preferable, and C.I. I. Pigment Yellow 129, 139, 150, 185 are more preferred, and C.I. I. Pigment Yellow 139, 150 and 185 are even more preferred.
Examples of the green dye include dyes whose hue is classified as green among the above dyes, and examples of the green pigment include pigments whose hue is classified as green among the above pigments.
Among the green pigments, phthalocyanine pigments are preferable, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable. I. At least one selected from the group consisting of Pigment Greens 7, 36, 58 and 59 is even more preferred.

The content of the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is the total amount of the pigment composition. It is 99.999% by mass or less, preferably 99.997% by mass or less, and more preferably 99.995% by mass or less.

The content of the quinophthalone compound is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 70% by mass, based on the total amount of the pigment composition. % Or less, preferably 60% by mass or less, and more preferably 50% by mass or less.

The content of the quinophthalone compound is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more with respect to 100 parts by mass of compound (I). It is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, and further preferably 50 parts by mass or less.

When the other colorant (A1-1) is contained, the content of the other colorant (A1-1) is 10 parts by mass or more with respect to 100 parts by mass in total of the compound (I) and the quinophthalone compound. It is preferably 50 parts by mass or more, more preferably 100 parts by mass or more, preferably 10,000 parts by mass or less, and more preferably 5000 parts by mass or less.

The total content of the compound (I) and the quinophthalone compound is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, still more preferably 2 parts by mass or more, based on 100 parts by mass of the pigment composition. Particularly preferably, it is 3 parts by mass or more.

<Isoindoline compounds other than the compounds represented by the formula (I)>
Examples of the isoindoline compound other than the compound represented by the formula (I) contained in the pigment composition of the present invention include isoindoline dyes and isoindoline pigments.
Specifically, known isoindoline yellow dyes described in Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Color Dyeing Co., Ltd.), Color Index (published by The Society of Dyers and Colorists), etc. The known isoindoline yellow pigments described in C.I. I. Pigment Yellow 139, 185 and other yellow pigments are more preferred. I. Pigment Yellow 185 is even more preferred.
The isoindoline compounds other than the compounds represented by the formula (I) may be used alone or in combination of two or more.

The pigment composition of the present invention contains a colorant other than the isoindoline compound other than the compound (I) and the compound represented by the formula (I) (hereinafter, may be referred to as a colorant (A1-2)). You may.

<Colorant (A1-2)>
The colorant (A1-2) may be a dye or a pigment.

As the dye, a known dye can be used, and examples thereof include dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). Further, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes and the like can be mentioned. These dyes may be used alone or in combination of two or more.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic green 1;
C. I. Bat green 1 etc.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). These can be used alone or in combination of two or more.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, Red pigments such as 268, 269, 273;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments;
C. I. Examples thereof include green pigments such as Pigment Green 7, 36, 58 and 59.

Other colorants (A1-2) include yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants"), green dyes and green pigments (hereinafter, these are collectively referred to as "yellow colorants"). (Sometimes referred to as a green colorant)) is preferred, yellow pigments and green pigments are more preferred, and green pigments are even more preferred.
Examples of the yellow dye include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.
Among the yellow pigments, quinophthalone yellow pigments and metal-containing yellow pigments are preferable, and C.I. I. Pigment Yellow 129, 138, 150 are more preferred, and C.I. I. Pigment Yellows 138 and 150 are even more preferred.
Examples of the green dye include dyes whose hue is classified as green among the above dyes, and examples of the green pigment include pigments whose hue is classified as green among the above pigments.
Among the green pigments, phthalocyanine pigments are preferable, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable. I. At least one selected from the group consisting of Pigment Greens 7, 36, 58 and 59 is even more preferred.

The content of the isoindoline compound other than the compound represented by the formula (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, and more preferably 0 in the total amount of the pigment composition. It is .005% by mass or more, the upper limit is 70% by mass or less, preferably 60% by mass or less, and more preferably 50% by mass or less.

The content of the isoindrin compound other than the compound represented by the formula (I) is preferably 0.01 part by mass or more, more preferably 0.1 part by mass with respect to 100 parts by mass of the compound (I). As mentioned above, it is more preferably 0.5 parts by mass or more, preferably 90 parts by mass or less, more preferably 70 parts by mass or less, still more preferably 50 parts by mass or less.

When the other colorant (A1-2) is contained, the content of the other colorant (A1-2) is 100% by mass in total of the isoindoline compound other than the compound (I) and the compound represented by the formula (I). It is preferably 10 parts by mass or more, more preferably 50 parts by mass or more, further preferably 100 parts by mass or more, preferably 10,000 parts by mass or less, and more preferably 5000 parts by mass or less. Is.

The total content of the isoindoline compounds other than the compound (I) and the compound represented by the formula (I) is preferably 0.5 parts by mass or more, more preferably 1 in 100 parts by mass of the pigment composition. It is by mass or more, more preferably 2 parts by mass or more, and particularly preferably 3 parts by mass or more.

<Green colorant>
The green colorant contained in the pigment composition of the present invention may be a green dye or a green pigment.
As the green dye, a known green dye can be used, and examples thereof include green dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Color Dyeing Co., Ltd.).
These dyes may be used alone or in combination of two or more.

Specific examples thereof include green dyes having the following color index (CI) numbers.
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic green 1;
C. I. Bat green 1 etc.

As the green pigment, known pigments can be used, and examples thereof include green pigments described in the Color Index (published by The Society of Dyers and Colorists).
These can be used alone or in combination of two or more.
Specifically, C.I. I. Examples thereof include green pigments such as Pigment Green 7, 36, 58 and 59.

As the green colorant contained in the pigment composition of the present invention, a green pigment is preferable. Among the green pigments, phthalocyanine pigments are preferable, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable. I. At least one selected from the group consisting of Pigment Greens 7, 36, 58 and 59 is even more preferred.

These green colorants may be used alone or in combination of two or more.

The pigment composition of the present invention may contain a colorant other than the compound (I) and the green colorant (hereinafter, may be referred to as a colorant (A1-3)).

<Colorant (A1-3)>
The colorant (A1-3) may be a dye or a pigment.

As the dye, a known dye can be used, and examples thereof include dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). Further, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes and the like can be mentioned. These dyes may be used alone or in combination of two or more.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60, etc.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). These can be used alone or in combination of two or more.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, Red pigments such as 268, 269, 273;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments can be mentioned.

As the other colorants (A1-3), yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants") are preferable, and yellow pigments are more preferable. Examples of the yellow dye include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.
Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments, and isoindoline yellow pigments are preferable, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185 are more preferred, and C.I. I. Pigment Yellow 138, 139, 150 and 185 are even more preferred.

The content of the green colorant is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 99 in the total amount of the pigment composition. It is .999% by mass or less, preferably 99.997% by mass or less, and more preferably 99.995% by mass or less.

The content of the green colorant is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more with respect to 100 parts by mass of compound (I). It is preferably 10000 parts by mass or less, more preferably 5000 parts by mass or less, and further preferably 4000 parts by mass or less.

When the other colorant (A1-3) is contained, the content of the other colorant (A1-3) is 100 parts by mass or less with respect to 100 parts by mass in total of the compound (I) and the green colorant. It is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, particularly preferably 50 parts by mass or less, preferably 0.001 part by mass or more, and more preferably 0. It is more than .003 parts by mass.

The total content of the compound (I) and the green colorant is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, still more preferably 80 parts by mass or more, and particularly preferably 80 parts by mass or more in 100 parts by mass of the pigment composition. It is preferably 90 parts by mass or more.

The coloring composition of the present invention contains a compound (I), a pigment composition containing a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green coloring agent, and a solvent (E).

<Solvent (E)>
The solvent (E) is, for example, an ester solvent (solvent containing -COO- in the molecule and not containing -O-), an ether solvent (solvent containing -O- in the molecule and not containing -COO-), and the like. Ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule) , -O-, -CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyletol, methyl anisol and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
Two or more of these solvents may be used in combination.
The content of the solvent (E) is preferably 40 to 99% by mass, more preferably 50 to 95% by mass, based on the total amount of the coloring composition.

In the coloring composition of the present invention, the pigment composition containing the compound (I), the quinophthalone compound, the isoindoline compound other than the compound represented by the formula (I), or the green coloring agent is dispersed in the solvent (E). It is preferable to have.

The pigment composition is, if necessary, treated with rosin, surface-treated with a derivative having an acidic group or a basic group introduced therein, grafted with a polymer compound or the like to the surface of the pigment composition, and atomized with sulfuric acid. A micronization treatment by a method or the like, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment of ionic impurities by an ion exchange method or the like may be performed. The particle size of the pigment composition is preferably substantially uniform. The pigment composition can be uniformly dispersed in the dispersion liquid by containing a dispersant and performing a dispersion treatment.

Examples of the dispersant include a surfactant and the like, and any of a cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (BASF Co., Ltd.), Azisper (registered trademark) (Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chemie Co., Ltd.), BYK (registered trademark) (Big Chemie Co., Ltd.), etc. Can be mentioned.

When a dispersant is used, the amount of the dispersant (solid content) used is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass or less, based on 100 parts by mass of the pigment composition. .. When the amount of the dispersant used is in the above range, a colored composition in a more uniform dispersed state tends to be obtained.

The content of the pigment composition in the coloring composition is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% of the total amount of the coloring composition. It is mass%.

The content of the pigment composition in the coloring composition is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, more preferably, with respect to the total amount of solid content. It is 2% by mass or more and 75% by mass or less.

The coloring composition of the present invention may contain a resin (hereinafter, may be referred to as a resin (B)). By containing the resin (B) in the coloring composition, the dispersion stability is further improved.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, and at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter referred to as "(a)"). It is more preferable that the polymer has a structural unit derived from (may be).
The resin (B) is a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, may be referred to as “(b)”), and others. It is preferably a copolymer having the structural unit of.
As another structural unit, the monomer (c) copolymerizable with the monomer (a) (however, different from the monomer (a) and the monomer (b); hereinafter “(c)”. A structural unit derived from (may be referred to as), a structural unit having an ethylenically unsaturated bond, and the like can be mentioned.

Examples of (a) include acrylic acid, methacrylic acid, crotonic acid and unsaturated monocarboxylic acids such as o-, m- and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexendicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, Bicyclounsaturated compounds containing carboxy groups such as 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene;
Carboxylic acid anhydrides such as the above unsaturated dicarboxylic acid anhydrides excluding fumaric acid and mesaconic acid;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher valent carboxylic acids such as monosuccinic acid mono [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerizability and solubility of the obtained resin in an alkaline aqueous solution.

(B) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
Examples of (b) include a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single having an oxetanyl group and an ethylenically unsaturated bond. A metric (b2) (hereinafter sometimes referred to as "(b2)") and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)") and the like. Can be mentioned.

As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)” may be used. There is) and a monomer (b1-2) having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter, may be referred to as “(b1-2)”).

As (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, and α-methylvinylbenzyl. Glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene , 2,3,4-Tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris Examples thereof include (glycidyloxymethyl) styrene and 2,4,6-tris (glycidyloxymethyl) styrene.
Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, seroxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth). Acrylic (eg, Cyclomer® A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer® M100; manufactured by Daicel Co., Ltd.), formula ( Examples thereof include a compound represented by BI) and a compound represented by the formula (BII).

[In the formula (BI) and the formula (BII), ^Ra and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. It may be replaced with.
X ^a and X ^b are each independently a single ^{bond, * - R c -, *} - R c -O -, * - represents the R ^c -S- or * -R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9) and the formula (BI-11) to the formula (BI-15). The compound represented by the formula (BI-1), the formula (BI-7), the formula (BI-9) and the compound represented by the formula (BI-15) are more preferable.

Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15), and among them, the formula (BII-1) and the formula are preferable. (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formulas (BII-11) to formulas (BII-15) are mentioned, and more. Preferred examples thereof include compounds represented by the formula (BII-1), the formula (BII-7), the formula (BII-9) and the formula (BII-15).

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination with the compound represented by the formula (BI) and the compound represented by the formula (BII). You may. When these are used in combination, the content ratio of the compound represented by the formula (BI) and the compound represented by the formula (BII) is on a molar basis, preferably 5:95 to 95: 5, and more preferably 10: It is 90 to 90:10, more preferably 20:80 to 80:20.

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decene-8-yl (meth) acrylate, tricyclo [5.2] 1.0 ^2,6 ] Decene-9-yl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) ) (Meta) acrylic acid esters such as acrylates, phenyl (meth) acrylates, naphthyl (meth) acrylates and benzyl (meth) acrylates;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-Phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5,6-bis (cyclohexyl) Bicyclounsaturated compounds such as oxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate and N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth) acrylamide. Vinyl group-containing amides such as; esters such as vinyl acetate; diene such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; and the like.
Of these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate, tricyclo [5.2.1. .0 ^2,6 ] Decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] Decene-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6} ] Decene-9-yl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene, benzyl (meth) acrylate and the like are preferable.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. A resin having such a structural unit has an ethylenically unsaturated bond in a polymer having a structural unit derived from (a) or (b) and a group capable of reacting with the group having (a) or (b). It can be obtained by adding a monomer having.
Such structural units include a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth) acrylate is added to a maleic anhydride unit, and glycidyl (meth). ) A structural unit in which (meth) acrylic acid is added to the acrylate unit can be mentioned. When these structural units have a hydroxy group, a structural unit to which a carboxylic acid anhydride is further added can also be mentioned as a structural unit having an ethylenically unsaturated bond.

The polymer having the structural unit derived from (a) can be produced, for example, by polymerizing the monomers constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent and the like are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) The solvent may be any one that dissolves each monomer.

As the obtained polymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or the polymer is taken out as a solid (powder) by a method such as reprecipitation. May be used.
If necessary, a reaction catalyst of a carboxylic acid or carboxylic acid anhydride and a cyclic ether (for example, tris (dimethylaminomethyl) phenol, etc.), a polymerization inhibitor (for example, hydroquinone, etc.) and the like may be used.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-Tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride and the like.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxytricyclo [5.2.1.0 ^2,6. ] Decyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth)
Acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^{2 , 6} ] Decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) ) Acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic Acid / vinyl toluene copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / 2-ethylhexyl (meth) acrylate copolymer, 3,4-Epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / tricyclo [5.2.1.0 ^2,6 ] decenyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acrylic loyloxymethyloxetane / (meth) acrylic acid / styrene copolymer, benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (Meta) acrylic acid copolymers and the resins described in JP-A-9-106071A, JP-A-2004-29518 and JP-A-2004-361455 can be mentioned.
Among them, as the resin (B), a copolymer containing a structural unit derived from (a) and a structural unit derived from (b) is preferable.
The resin (B) may be a combination of two or more, in which case the resin (B) is at least 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate. / (Meta) acrylic acid copolymer; 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (Meta) acrylate copolymer; 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer; 3,4-epoxy It preferably contains one or more selected from the tricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylate / 2-ethylhexyl (meth) acrylate copolymer.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, still more preferably 5,000 to 30, It is 000. The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The acid value (solid content conversion value) of the resin (B) is preferably 10 to 300 mg-KOH / g, more preferably 20 to 250 mg-KOH / g, and further preferably 30 to 200 mg-KOH / g. .. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) in the coloring composition is preferably 3 to 99% by mass, more preferably 5 to 99% by mass, and further preferably 7 to 95% by mass with respect to the total amount of solid content. %.

The coloring composition of the present invention may contain a coloring agent (hereinafter, may be referred to as a coloring agent (A2)). The colorant (A2) may contain one kind or two or more kinds of colorants. The colorant (A2) preferably contains compound (I), a yellow colorant or a green colorant.

<Colorant (A2)>
The colorant (A2) may be a dye or a pigment. As the dye, a known dye can be used, and examples thereof include dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). Further, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes and the like can be mentioned. These dyes may be used alone or in combination of two or more.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic green 1;
C. I. Bat green 1 etc.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). These can be used alone or in combination of two or more.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, Red pigments such as 268, 269, 273;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments;
C. I. Examples thereof include green pigments such as Pigment Green 7, 36, 58 and 59.

Other colorants (A2) include compound (I), yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow colorants"), green dyes and green pigments (hereinafter, these are collectively referred to). (Sometimes referred to as a “green colorant”), the compound (I), the yellow pigment and the green pigment are more preferable, and the compound (I) and the green pigment are further preferable.
Examples of the yellow dye include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.
Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments, and isoindoline yellow pigments are preferable, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185 are more preferred, and C.I. I. Pigment Yellow 138, 139, 150 and 185 are even more preferred.
Examples of the green dye include dyes whose hue is classified as green among the above dyes, and examples of the green pigment include pigments whose hue is classified as green among the above pigments.
Among the green pigments, phthalocyanine pigments are preferable, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable. I. At least one selected from the group consisting of Pigment Greens 7, 36, 58 and 59 is even more preferred.

When the coloring composition of the present invention contains a coloring agent (A2), a colorant (A2) -containing liquid containing the coloring agent (A2) and the solvent (E) is prepared in advance, and then the coloring agent (A2) is contained. The liquid may be used to prepare the coloring composition. When the colorant (A2) is insoluble in the solvent (E), the colorant (A2) -containing liquid can be prepared by dispersing the colorant (A2) in the solvent (E) and mixing. The colorant (A2) -containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.

The coloring composition of the present invention comprises a pigment composition containing a compound represented by the formula (I), an isoindoline compound other than the quinophthalone compound and the compound represented by the formula (I), or a green colorant, and a solvent (E). ) And the colorant (A2) -containing liquid containing the colorant (A2) and the solvent (E) are preferably mixed. The production method includes a compound represented by the formula (I), a pigment composition containing an isoindoline compound other than the compound represented by the formula (I) or a green colorant, and a solvent (E). Is mixed with a bead mill or the like to prepare a coloring composition, and a method of mixing the obtained coloring composition with a colorant (A2) -containing liquid containing a colorant (A2) and a solvent (E) is preferable.

The colorant (A2) is preferably a colorant containing at least one selected from the compound represented by the formula (I), the green colorant, and the yellow colorant.

The colorant (A2) is treated with a rosin, a surface treatment using a colorant derivative having an acidic group or a basic group introduced therein, and a graft treatment on the surface of the colorant (A2) with a polymer compound or the like, if necessary. , Aluminization treatment by a sulfuric acid atomization method or the like, cleaning treatment with an organic solvent or water for removing impurities, removal treatment by an ion exchange method of ionic impurities or the like may be performed. The particle size of the colorant (A2) is preferably substantially uniform. The colorant (A2) can be uniformly dispersed in the colorant (A2) -containing liquid by carrying out the dispersion treatment by containing the dispersant. The colorant (A2) may be dispersed alone or a plurality of types may be mixed and dispersed.

Examples of the dispersant include a surfactant and the like, and any of a cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (BASF Co., Ltd.), Azisper (registered trademark) (Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chemie Co., Ltd.), BYK (registered trademark) (Big Chemie Co., Ltd.), etc. Can be mentioned.

When a dispersant is used to prepare the colorant (A2) -containing liquid, the amount of the dispersant (solid content) used is preferably 300 parts by mass or less with respect to 100 parts by mass of the colorant (A2). Yes, more preferably 5 parts by mass or more and 100 parts by mass or less. When the amount of the dispersant used is within the above range, there is a tendency to obtain a colorant (A2) -containing liquid in a more uniform dispersed state.

The content of the colorant (A2) in the colorant (A2) -containing liquid is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, based on the total amount of the colorant (A2) -containing liquid. It is more preferably 1 to 40% by mass.

The content of the colorant (A2) in the colorant (A2) -containing liquid is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, based on the total amount of solid content. Yes, more preferably 2% by mass or more and 75% by mass or less.

The coloring composition of the present invention contains a resin (B), and after preparing a colorant (A2) -containing liquid containing the colorant (A2) and the solvent (E) in advance, the colorant (A2) -containing liquid is prepared. When preparing a coloring composition using the above, the coloring agent (A2) -containing liquid may contain a part or all, preferably a part of the resin (B) contained in the coloring composition in advance. By including the resin (B) in advance, the dispersion stability of the colorant (A2) -containing liquid can be further improved.
The content of the resin (B) in the colorant (A2) -containing liquid is, for example, 1 to 500 parts by mass, preferably 5 to 200 parts by mass with respect to 100 parts by mass of the colorant (A2). More preferably, it is 10 to 100 parts by mass.

In the coloring composition, the content of the coloring agent (A) including the pigment composition and the coloring agent (A2) is usually 1% by mass or more and 90% by mass or less, preferably 90% by mass or less, based on the total amount of solid content. It is 1% by mass or more and 80% by mass or less, and more preferably 2% by mass or more and 75% by mass or less.
The content of the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, based on the total amount of the colorant (A). Is 99.999% by mass or less, preferably 99.997% by mass or less, and more preferably 99.995% by mass or less.

The content of the quinophthalone compound is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 70 in the total amount of the colorant (A). It is 0% by mass or less, preferably 60% by mass or less, and more preferably 50% by mass or less.
The content of the quinophthalone compound is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more with respect to 100 parts by mass of compound (I). It is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, and further preferably 50 parts by mass or less.
When the other colorant (A2) is contained, the content of the other colorant (A2) is preferably 10 parts by mass or more with respect to 100 parts by mass in total of the compound (I) and the quinophthalone compound. It is preferably 50 parts by mass or more, more preferably 100 parts by mass or more, preferably 10,000 parts by mass or less, and more preferably 5000 parts by mass or less.
The total content of the compound (I) and the quinophthalone compound is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and further preferably 2 parts by mass in 100 parts by mass of the colorant (A). The above is particularly preferably 3 parts by mass or more.

The content of the isoindoline compound other than the compound represented by the formula (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.003% by mass or more, based on the total amount of the colorant (A). It is 0.005% by mass or more, the upper limit is 70% by mass or less, preferably 60% by mass or less, and more preferably 50% by mass or less.
The content of the isoindrin compound other than the compound represented by the formula (I) is preferably 0.01 part by mass or more, more preferably 0.1 part by mass with respect to 100 parts by mass of the compound (I). As mentioned above, it is more preferably 0.5 parts by mass or more, preferably 90 parts by mass or less, more preferably 70 parts by mass or less, still more preferably 50 parts by mass or less.
When the other colorant (A2) is contained, the content of the other colorant (A2) is 100 parts by mass in total of the isoindoline compound other than the compound (I) and the compound represented by the formula (I). It is preferably 10 parts by mass or more, more preferably 50 parts by mass or more, further preferably 100 parts by mass or more, preferably 10,000 parts by mass or less, and more preferably 5000 parts by mass or less.
The total content of the isoindoline compounds other than the compound (I) and the compound represented by the formula (I) is preferably 0.5 parts by mass or more, more preferably 0.5 part by mass or more, based on 100 parts by mass of the colorant (A). Is 1 part by mass or more, more preferably 2 parts by mass or more, and particularly preferably 3 parts by mass or more.

The content of the green colorant is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is the total amount of the colorant (A). It is 99.999% by mass or less, preferably 99.997% by mass or less, and more preferably 99.995% by mass or less.
The content of the green colorant is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more with respect to 100 parts by mass of compound (I). It is preferably 10000 parts by mass or less, more preferably 5000 parts by mass or less, and further preferably 4000 parts by mass or less.
When the other colorant (A2) is contained, the content of the other colorant (A2) is preferably 10,000 parts by mass or less with respect to 100 parts by mass in total of the compound (I) and the green colorant. It is more preferably 5000 parts by mass or less, further preferably 4000 parts by mass or less, preferably 0.001 parts by mass or more, and even more preferably 0.003 parts by mass or more.

The color-curable composition of the present invention is a pigment composition containing the compound (I), a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green colorant, a solvent (E), and a polymerizable composition. Contains compound (C).

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferable. It is a (meth) acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Etc., as well as the above-mentioned monomers (a), monomer (b) and monomer (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Above all, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl ) Isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate, preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 1 to 65% by mass, more preferably 3 to 60% by mass, based on the total amount of solids in the color-curable composition. It is more preferably ~ 55% by mass.

The color curable composition of the present invention may contain a polymerization initiator (D).

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, an acylphosphine oxide compound and the like.

Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-. 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl)- 3-Cyclopentylpropane-1-on-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl -6- (2-methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl) -2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazole-3-yl] -3-cyclopentylpropane-1-imine and N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3- Cyclopentylpropane-1-one-2-imine and the like can be mentioned. Further, as the O-acyloxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF Corporation) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, as the O-acyloxym compound, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- At least one selected from the group consisting of 1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyl is preferable. Oxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-. Examples thereof include on and 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one. As the alkylphenone compound, a commercially available product such as Irgacure 369, 907, 379 (all manufactured by BASF Corporation) may be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, and Also included are 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one oligomers, α, α-diethoxyacetophenone and benzyldimethylketal.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl) -4. , 4', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4, 4', 5,5'-Tetraphenyl biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole 2-Chlorophenyl) -4,4', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxy) Phenyl) Biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.) and the phenyl group at the 4,4', 5,5'-position are substituted with a carboalkoxy group. Examples thereof include imidazole compounds (see, for example, Japanese Patent Laid-Open No. 7-10913).

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl). -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl)- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methyl) Phenyl) ethenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine and the like can be mentioned. ..

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, o-methyl benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzoyl compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthlenquinone, Kinon compounds such as 2-ethylanthraquinone and camphorquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate and titanosen compounds.
These are preferably used in combination with the polymerization initiation aid (D1) (particularly amines) described later.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably. A polymerization initiator containing an O-acyloxime compound.

The content of the polymerization initiator (D) is preferably 0.001 to 40% by mass, more preferably 0.01 to 30% by mass, based on the total amount of solids in the color-curable composition.

The color curable composition of the present invention may contain a polymerization initiation aid (D1).

<Polymerization initiation aid (D1)>
The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4-. 2-Ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone and 4,4'-bis ( Ethylmethylamino) benzophenone and the like, preferably 4,4'-bis (diethylamino) benzophenone and the like. Further, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, and N. -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.

When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.001 to 30% by mass, more preferably 0.01 to 30% by mass, based on the total amount of solids in the color-curable composition. It is 20% by mass.

The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.

<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK) and the like. ..

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafuck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content thereof is usually 0.0005% by mass or more and 1% by mass or less, preferably 0.001% by mass or more and 0.5% by mass, based on the total amount of the coloring composition. % Or less, more preferably 0.001% by mass or more and 0.2% by mass or less, further preferably 0.002% by mass or more and 0.1% by mass or less, and particularly preferably 0.005% by mass or more. It is 0.1% by mass or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Antioxidant>
From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more. The antioxidant is not particularly limited as long as it is an industrially generally used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant and the like can be used.

Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF Co., Ltd.). Irganox 1076 (Irganox 1076: octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF Co., Ltd.), Irganox 1330 (Irganox 1330: 3,3', 3', ', 5,5', 5''-Hexa-tert-butyl-a, a', a''- (methitylen-2,4,6-triyl) tri-p-cresol, manufactured by BASF Co., Ltd., Irganox 3114 (Irganox 3114: 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) ) -Trion, manufactured by BASF Co., Ltd., Irganox 3790 (Irganox 3790: 1,3,5-tris ((4-tert-butyl-3-hydroxy-2,6-xylyl) methyl) -1,3. 5-Triazine-2,4,6 (1H, 3H, 5H) -Torion, manufactured by BASF Co., Ltd., Irganox 1035 (Irganox 1035: Thiodiethylenebis [3- (3,5-di-tert-butyl-) 4-Hydroxyphenyl) propionate], BASF Co., Ltd.), Irganox 1135: benzenepropanoic acid, 3,5-bis (1,1-dimethylethyl) -4-hydroxy, C7-C9 side chain alkyl Estel, manufactured by BASF Co., Ltd., Irganox 1520L (Irganox 1520L: 4,6-bis (octylthiomethyl) -o-cresol, manufactured by BASF Co., Ltd.), Irganox 3125 (Irganox 3125, manufactured by BASF Co., Ltd.) ), Irganox 565: 2,4-bis (n-octylthio) -6- (4-hydroxy 3', 5'-di-tert-butylanilino) -1,3,5-triazine, BASF (strain). ), Adecastab AO-80 (Adecastab AO-80: 3,9-bis (2- (3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy) -1,1-dimethyl) Ethyl) -2,4,8,10-tetraoxaspiro (5, 5) Undecan, manufactured by ADEKA Corporation, Sumilizer BHT (manufactured by Sumitomo Chemical Co., Ltd.), Sumitomo GA-80 (manufactured by Sumitomo Chemical Co., Ltd.), Sumitomo GS (Sumilizer GS, Sumitomo Chemical Co., Ltd.) Examples thereof include Cyanox 1790 (manufactured by Cyanox 1790, manufactured by Cytec Co., Ltd.) and Vitamin E (manufactured by Eisai Corporation).

Examples of the phosphorus-based antioxidant include Irgafos 168 (Irgafos 168: Tris (2,4-di-tert-butylphenyl) phosfite, manufactured by BASF Co., Ltd.), Irgafos 12: Tris [2- [[2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphin-6-yl] oxy] ethyl] amine, manufactured by BASF Co., Ltd.), Irgafos 38: bis (2,4-bis (1,1-dimethylethyl) -6-methylphenyl) ethyl ester phosphite, BASF Co., Ltd.), ADEKA STAB 329K (ADEKA Co., Ltd.), Adeka Stub PEP36 (manufactured by ADEKA Co., Ltd.), Adeka Stub PEP-8 (manufactured by ADEKA Co., Ltd.), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (manufactured by Weston 618, GE), Weston 619G (Weston 619G, GE) , Ultraknox 626 (Ultranox 626, manufactured by GE) and Sumilizer GP: 6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy] -2,4 8,10-Tetra-tert-butyldibenz [d, f] [1.3.2] dioxaphosphepine) (manufactured by Sumitomo Chemical Co., Ltd.) and the like can be mentioned.

Examples of the sulfur-based antioxidant include β-alkyl mercaptopropion of a dialkylthiodipropionate compound such as dilauryl thiodipropionate, dimyristyl or distearyl, and a polyol such as tetrakis [methylene (3-dodecylthio) propionate] methane. Examples thereof include acid ester compounds.

<Other ingredients>
If necessary, the coloring composition of the present invention may contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and the like.
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycid. Xipropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3- Methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isoxapropyltriethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N- 2- (Aminoethyl) -3-aminopropylmethyldiethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane , 3-Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, and the like.

<Color filter>
A color filter can be formed from the coloring composition or the coloring curable composition of the present invention. Examples of the method for forming the colored pattern include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable. The photolithography method is a method in which the color-curable composition is applied to a substrate and dried to form a color-curable composition layer, and the color-curable composition layer is exposed and developed through a photomask. Is. In the photolithography method, it is preferable that the color-curable composition contains the polymerization initiator (D). In the photolithography method, a colored coating film which is a cured product of the colored curable composition layer can be formed by not using a photomask at the time of exposure and / or not developing the photomask. The colored pattern or colored coating film thus formed can be used as the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, it is 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.1 to 20 μm. Is 0.5 to 6 μm.

As the substrate, a glass plate, a resin plate, silicon, or a substrate on which an aluminum, silver, silver / copper / palladium alloy thin film, or the like is formed is used. Another color filter layer, resin layer, transistor, circuit and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.
First, the color-curable composition is applied onto a substrate and dried by heat drying (pre-baking) and / or vacuum drying to remove volatile components such as a solvent to obtain a smooth color-curable composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.

The color curable composition layer is then exposed via a photomask to form the desired color pattern. Since it is possible to uniformly irradiate the entire exposed surface with parallel light rays and accurately align the photomask with the substrate on which the colored curable composition layer is formed, an exposure device such as a mask aligner and a stepper can be used. It is preferable to use it.

A colored pattern is formed on the substrate by developing the colored curable composition layer after exposure by contacting it with a developing solution. By development, the unexposed portion of the color-curable composition layer is dissolved in a developer and removed.
As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide is preferable.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
The developed substrate is preferably washed with water.
Further, it is preferable to post-bake the obtained coloring pattern.

The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image sensor, and particularly as a color filter used in a liquid crystal display device.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples as well as the present invention, and appropriate modifications are made to the extent that it can meet the purposes of the preceding and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention. In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass".

In the following synthetic examples, the structure of the compound was confirmed by NMR (JMM-ECA-500; manufactured by JEOL Ltd.) or mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD6130 type).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40 ° C
Solvent: Tetrahydrofuran Flow rate: 1.0 mL / min Solid content concentration of analytical sample: 0.001-0.01 mass%
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight (Mw) and the number average molecular weight (Mn) obtained above was defined as the degree of dispersion.

Synthesis example 1
11.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 91.5 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 2 ° C., a mixture of 8.59 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 77.6 parts of methanol was applied over 1 hour and 45 minutes. Was added dropwise, and the mixture was stirred at 2 ° C. for 6 hours and 40 minutes. To the obtained mixture, 4.18 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 2 ° C. for 1 hour and 45 minutes. 17.0 parts of acetic acid was added while keeping the temperature of the obtained mixture below 4 ° C. To the obtained mixture, 23.9 parts of pivaloyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 87 hours. To the obtained mixture, 10.8 parts of pivaloyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 5.40 parts of acetic acid were added, and the mixture was stirred at 40 ° C. for 4 hours and 30 minutes. The resulting mixture was filtered and the residue was washed with 360 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 22.8 parts of the compound (Compound 101) represented by the formula (I-1).

<Identification of compound represented by formula (I-1) (Compound 101)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 362
Exact Mass: 361

Synthesis example 2
2.59 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 24.1 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 2 ° C., a mixture of 1.50 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 23.2 parts of methanol was added to this mixture. The mixture was added dropwise over 1 hour and 10 minutes. The resulting mixture was stirred at 2 ° C. for 2 hours and 20 minutes. While keeping the temperature of the obtained mixture at 3 ° C. or lower, 2.35 parts of acetic acid was added, and then 4.13 parts of pivaloyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added. The resulting mixture was stirred at room temperature for 3 hours and 35 minutes and at 40 ° C. for 1 hour and 45 minutes. To the obtained mixture, 4.16 parts of pivaloyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 ° C. for 1 hour and 30 minutes. The resulting mixture was stirred at room temperature for 37 hours. To the obtained mixture, 1.89 parts of pivaloyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.24 parts of acetic acid were added, and the mixture was stirred at 40 ° C. for 5 hours and 15 minutes. The resulting mixture was filtered and the residue was washed with 198 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 5.58 parts of the compound (Compound 188) represented by the formula (I-2).

<Identification of the compound represented by the formula (I-2) (Compound 188)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 407
Exact Mass: 406

Synthesis example 3
7.02 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 61.6 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 2 ° C., a mixture of 8.20 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.6 parts of methanol was mixed for 1 hour and 30 minutes. Dropped over. The resulting mixture was stirred at 2 ° C. for 6 hours and 15 minutes. 10.7 parts of acetic acid was added while keeping the temperature of the obtained mixture below 4 ° C. To the obtained mixture, 17.6 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 44 hours. The resulting mixture was filtered and the residue was washed with 800 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 18.0 parts of the compound (Compound 102) represented by the formula (I-3).

<Identification of compound represented by formula (I-3) (Compound 102)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 402
Exact Mass: 401

Synthesis example 4
4.12 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 37.2 parts of methanol were mixed. While keeping the temperature of this mixture at 2 ° C., a mixture of 4.82 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 45.2 parts of methanol was added to this mixture for 1 hour. Dropped over. The resulting mixture was stirred at 2 ° C. for 6 hours. 6.29 parts of acetic acid was added while keeping the temperature of the obtained mixture below 4 ° C. To the obtained mixture, 12.7 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 2 ° C. for 1 hour and at room temperature for 20 minutes. The obtained mixture was stirred at 40 ° C. for 2 hours, at room temperature for 11 hours, and further at 40 ° C. for 5 hours and 40 minutes. 3.18 parts of acetic acid and 6.45 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture. The resulting mixture was stirred at 40 ° C. for 4 hours and at room temperature for 62 hours. The resulting mixture was filtered and the residue was washed 3 times with the same volume of methanol as the residue. The obtained residue was recrystallized from N, N-dimethylformamide. The obtained crystals were dried under reduced pressure at 60 ° C. to obtain 9.99 parts of the compound (Compound 112) represented by the formula (I-4).

<Identification of compound represented by formula (I-4) (Compound 112)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469

Synthesis example 5
4.07 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 36.0 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 2 ° C., a mixture of 4.76 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 44.3 parts of methanol was mixed for 1 hour and 10 minutes. Dropped over. The resulting mixture was stirred at 2 ° C. for 5 hours and 25 minutes. 6.23 parts of acetic acid was added while keeping the resulting mixture below 3 ° C. To the obtained mixture, 12.6 parts of 4-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 ° C. for 40 minutes. 456 parts of methanol was added to the obtained mixture, and the mixture was stirred at 40 ° C. for 3 hours and at room temperature for 37 hours. To the obtained mixture, 3.14 parts of acetic acid, 6.31 parts of 4-chlorobenzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 124 parts of methanol were added, and the mixture was stirred at 40 ° C. for 6 hours and 40 minutes. The resulting mixture was stirred at room temperature for 18 hours. The resulting mixture was filtered and the residue was washed with 554 parts of methanol. To the obtained residue, 1740 parts of N, N-dimethylformamide was added, the mixture was stirred at 80 ° C., and then filtered while keeping the temperature at 80 ° C. A residue and a filtrate (ROE-1) were obtained. The obtained residue was washed with 150 parts of N, N-dimethylformamide. A residue and a washing liquid (SEN-1) were obtained. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 4.88 parts of the compound (Compound 114) represented by the formula (I-5). The obtained filtrate (ROE-1) and washing solution (SEN-1) were combined and allowed to stand at room temperature for 12 hours. The resulting mixture was filtered and the residue was washed 3 times with the same volume of N, N-dimethylformamide as the residue. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 5.16 parts of the compound (Compound 114) represented by the formula (I-5).

<Identification of compound represented by formula (I-5) (compound 114)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469

Synthesis example 6
10.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 93 parts of methanol were mixed. A mixture of 11.7 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 110 parts of methanol was added dropwise to the obtained mixture at 2 ° C. over 1 hour and 15 minutes. did. The resulting mixture was stirred at 5 ° C. for 3 hours. 7.71 parts of acetic acid and 8 parts of methanol were added to the obtained mixture while keeping the temperature below 5 ° C. To the obtained mixture, 11.4 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added. The obtained mixture was stirred at 2 ° C. for 40 minutes and then at room temperature for 17 hours and 40 minutes. 109 parts of methanol was added to the obtained mixture, and the mixture was stirred at room temperature for 1 hour and 20 minutes. To the resulting mixture was added 6.41 parts acetic acid, 10.1 parts barbituric acid and 16.0 parts methanol. The obtained mixture was stirred at room temperature for 5 hours and then at 40 ° C. for 2 hours. 344 parts of water was added to the resulting mixture. The obtained mixture was stirred at 40 ° C. for 3 hours and 25 minutes, and then stirred at room temperature for 16 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 1.55 parts of a compound (Compound 466) represented by the formula (I-6).

<Identification of compound represented by formula (I-6) (Compound 466)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 385
Exact Mass: 384

Synthesis example 7
5.00 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 42.0 parts of methanol were mixed. While keeping the temperature at 2 ° C., a mixture of 5.83 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 52.5 parts of methanol was added to the obtained mixture over 1 hour and 30 minutes. Dropped. The resulting mixture was stirred at 2 ° C. for 6 hours. While keeping the temperature below 4 ° C., 7.59 parts of acetic acid was added to the obtained mixture, and 17.4 parts of methyl 4-cyanoacetylbenzoate (synthesized according to the method described in JP-A-8-176154). And 682 parts of methanol were added. The obtained mixture was stirred at room temperature for 4 hours and then at 40 ° C. for 48 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 2.21 parts of a compound represented by the formula (I-7) (Compound 139).

<Identification of compound represented by formula (I-7) (Compound 139)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 518
Exact Mass: 517

Synthesis example 8
4.10 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 69.0 parts of methanol were mixed. A mixture of 4.68 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 45.0 parts of methanol was added dropwise to the obtained mixture over 50 minutes while keeping the temperature at 2 ° C. .. The resulting mixture was stirred at 2 ° C. for 2 hours and 30 minutes. While keeping the temperature at 2 ° C., 7.35 parts of acetic acid and 18.7 parts of phenylsulfonyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture. The obtained mixture was stirred at room temperature for 15 hours and then at 40 ° C. for 50 hours. The obtained mixture was divided in half to obtain a mixture 1 and a mixture 2.

After distilling off the solvent of the mixture 1 with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.0273 parts of the compound (Compound 270) represented by the formula (I-8).
To the mixture 2, 2.00 parts of acetic acid, 3.02 parts of barbituric acid, 50 parts of methanol and 102 parts of water were added, and the mixture was stirred at 40 ° C. for 12 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.0313 parts of a compound (Compound 634) represented by the formula (I-9).

<Identification of compound represented by formula (I-8) (Compound 270)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 519
Exact Mass: 518
<Identification of compound represented by formula (I-9) (Compound 634)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 466
Exact Mass: 465

Synthesis example 9
In the same manner as in Synthesis Example 7, the formula (I-10) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 3-chlorobenzoylacetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (compound 113) was obtained.

<Identification of compound represented by formula (I-10) (Compound 113)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469

Synthesis example 10
The compound represented by the formula (I-11) (Compound 138) is the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate is replaced with methyl 3-cyanoacetylbenzoate while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-11) (Compound 138)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 518
Exact Mass: 517

Synthesis example 11
It is represented by the formula (I-12) in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with phenylsulfonyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining its molar ratio. Compound (Compound 183) was obtained.

<Identification of compound represented by formula (I-12) (Compound 183)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 474
Exact Mass: 473

Synthesis example 12
In the same manner as in Synthesis Example 7, the formula (I-13) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 2-methylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 103) was obtained.

<Identification of compound represented by formula (I-13) (Compound 103)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 430
Exact Mass: 429

Synthesis example 13
In the same manner as in Synthesis Example 7, the formula (I-14) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 3-methylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 104) was obtained.

<Identification of compound represented by formula (I-14) (Compound 104)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 430
Exact Mass: 429

Synthesis example 14
In the same manner as in Synthesis Example 7, the formula (I-15) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 4-methylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 105) was obtained.

<Identification of compound (Compound 105) represented by formula (I-15)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 430
Exact Mass: 429

Synthesis example 15
The compound represented by the formula (I-16) (Compound 140) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-nitrobenzoylacetonitrile while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-16) (Compound 140)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 492
Exact Mass: 491

Synthesis example 16
The compound (Compound 141) represented by the formula (I-17) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-nitrobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-17) (compound 141)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 492
Exact Mass: 491

Synthesis example 17
The compound (Compound 142) represented by the formula (I-18) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-nitrobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound (Compound 142) represented by formula (I-18)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 492
Exact Mass: 491

Synthesis example 18
The compound (Compound 121) represented by the formula (I-19) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-cyanobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-19) (Compound 121)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 452
Exact Mass: 451

Synthesis example 19
The compound represented by the formula (I-20) (Compound 147) is the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate is replaced with 3-dimethylaminobenzoyl acetonitrile while maintaining its molar ratio. Got

<Identification of compound represented by formula (I-20) (Compound 147)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 488
Exact Mass: 487

Synthesis example 20
The compound (Compound 165) represented by the formula (I-21) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 1-naphthoyl acetonitrile while maintaining its molar ratio. Obtained.

<Identification of the compound represented by the formula (I-21) (Compound 165)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 502
Exact Mass: 501

Synthesis example 21
The compound (Compound 166) represented by the formula (I-22) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 2-naphthoyl acetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-22) (Compound 166)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 502
Exact Mass: 501

Synthesis example 22
The compound represented by the formula (I-23) (Compound 106) is the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate is replaced with 2-trifluoromethylbenzoyl acetonitrile while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-23) (Compound 106)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 538
Exact Mass: 537

Synthesis example 23
The formula (I-24) was the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-trifluoromethylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-24) (Compound 107)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 538
Exact Mass: 537

Synthesis example 24
The formula (I-25) was the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-trifluoromethylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-25) (Compound 108)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 538
Exact Mass: 537

Synthesis example 25
In the same manner as in Synthesis Example 7, the formula (I-26) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 2-fluorobenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 109) was obtained.

<Identification of compound represented by formula (I-26) (Compound 109)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 438
Exact Mass: 437

Synthesis example 26
The compound (Compound 110) represented by the formula (I-27) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-fluorobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-27) (Compound 110)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 438
Exact Mass: 437

Synthesis example 27
In the same manner as in Synthesis Example 7, the formula (I-28) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 4-fluorobenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 111) was obtained.

<Identification of compound represented by formula (I-28) (Compound 111)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 438
Exact Mass: 437

Synthesis example 28
The compound (Compound 115) represented by the formula (I-29) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 2-bromobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-29) (Compound 115)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 558
Exact Mass: 557

Synthesis example 29
The compound (Compound 116) represented by the formula (I-30) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-bromobenzoylacetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound (Compound 116) represented by formula (I-30)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 558
Exact Mass: 557

Synthesis example 30
In the same manner as in Synthesis Example 7, the formula (I-31) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 4-bromobenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 117) was obtained.

<Identification of compound represented by formula (I-31) (Compound 117)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 558
Exact Mass: 557

Synthesis example 31
The compound (Compound 125) represented by the formula (I-32) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 2-methoxybenzoyl acetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-32) (Compound 125)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 462
Exact Mass: 461

Synthesis example 32
The compound (Compound 126) represented by the formula (I-33) was prepared in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-methoxybenzoyl acetonitrile while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-33) (Compound 126)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 462
Exact Mass: 461

Synthesis example 33
In the same manner as in Synthesis Example 7, the formula (I-34) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 4-methoxybenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 127) was obtained.

<Identification of compound represented by formula (I-34) (Compound 127)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 462
Exact Mass: 461

Synthesis example 34
13.8 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 115 parts of methanol were mixed. While keeping the temperature at 2 to 3 ° C., a mixture of 7.94 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.0 parts of methanol was sprinkled on the obtained mixture for 40 minutes. And dropped. The resulting mixture was stirred at 2-3 ° C. for 4 hours. While keeping the obtained mixture at 3 ° C. or lower, 12.5 parts of acetic acid was added, and then 25.4 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 150 parts of methanol were added. The obtained mixture was stirred at room temperature for 18 hours and then at 43 ° C. for 5 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 1.02 part of a compound (Compound 189) represented by the formula (I-35).

<Identification of compound (Compound 189) represented by formula (I-35)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 447
Exact Mass: 446

Synthesis example 35
The formula (I-36) was the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3,4-dichlorobenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. ) Was obtained.

<Identification of compound (Compound 118) represented by formula (I-36)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 538
Exact Mass: 537

Synthesis example 36
Synthetic Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio (5,6,7,8-tetrahydro-2-naphthoyl). Similarly, a compound represented by the formula (I-37) (Compound 167) was obtained.

<Identification of compound represented by formula (I-37) (Compound 167)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 510
Exact Mass: 509

Synthesis example 37
The formula (I-38) was the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-dimethylaminobenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The compound represented by (Compound 148) was obtained.

<Identification of compound represented by formula (I-38) (Compound 148)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 488
Exact Mass: 487

Synthesis example 38
It is represented by the formula (I-39) in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with methylsulfonylacetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. Compound (Compound 182) was obtained.

<Identification of compound represented by formula (I-39) (Compound 182)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 350
Exact Mass: 349

Synthesis example 39
The formula (I-) was the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with (4-bromophenylsulfonyl) acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. A compound represented by 40) (Compound 184) was obtained.

<Identification of compound (Compound 184) represented by formula (I-40)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 630
Exact Mass: 629

Synthesis example 40
The compound (compound) represented by the formula (I-41) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with methyl 2-cyanoacetylbenzoate while maintaining its molar ratio. 137) was obtained.

<Identification of compound represented by formula (I-41) (Compound 137)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 518
Exact Mass: 517

Synthesis example 41
The compound (compound) represented by the formula (I-42) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-sulfamoylbenzoylacetonitrile while maintaining its molar ratio. 157) is obtained.

Synthesis example 42
The compound represented by the formula (I-43) (Compound 134) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio. ) Was obtained.

<Identification of compound (Compound 134) represented by formula (I-43)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489

Synthesis example 43
The compound represented by the formula (I-44) (Compound 135) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-44) (Compound 135)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489

Synthesis example 44
The compound represented by the formula (I-45) (Compound 136) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-cyanoacetylbenzoic acid while maintaining its molar ratio. ) Was obtained.

<Identification of compound represented by formula (I-45) (Compound 136)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489

Synthesis example 45
The compound represented by the formula (I-46) (Compound 120) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-cyanobenzoylacetonitrile while maintaining its molar ratio. To get.

Synthesis example 46
The compound represented by the formula (I-47) (Compound 122) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-hydroxybenzoylacetonitrile while maintaining its molar ratio. Got

<Identification of compound (Compound 122) represented by formula (I-47)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 434
Exact Mass: 433

Synthesis example 47
The compound represented by the formula (I-48) (Compound 123) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-hydroxybenzoylacetonitrile while maintaining its molar ratio. Got

<Identification of compound (Compound 123) represented by formula (I-48)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 434
Exact Mass: 433

Synthesis example 48
The compound represented by the formula (I-49) (Compound 124) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-hydroxybenzoylacetonitrile while maintaining its molar ratio. Got

<Identification of compound represented by formula (I-49) (Compound 124)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 434
Exact Mass: 433

Synthesis example 49
The compound represented by the formula (I-50) (Compound 143) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-aminobenzoylacetonitrile while maintaining its molar ratio. To get.

Synthesis example 50
The compound represented by the formula (I-51) (Compound 144) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-aminobenzoyl acetonitrile while maintaining its molar ratio. To get.

Synthesis example 51
The compound represented by the formula (I-52) (Compound 145) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-aminobenzoylacetonitrile while maintaining its molar ratio. To get.

Synthesis example 52
The compound represented by the formula (I-53) (Compound 133) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-acetylbenzoylacetonitrile while maintaining its molar ratio. Got

<Identification of compound represented by formula (I-53) (Compound 133)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 486
Exact Mass: 485

Synthesis example 53
The compound represented by the formula (I-54) (Compound 151) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-diethylaminobenzoyl acetonitrile while maintaining its molar ratio. To get.

Synthesis example 54
The compound represented by the formula (I-55) (Compound 130) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-methylthiobenzoyl acetonitrile while maintaining its molar ratio. To get.

Synthesis example 55
The compound represented by the formula (I-56) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with acetonitrile (4-acetylaminophenylsulfonyl) while maintaining its molar ratio. (Compound 185) is obtained.

Synthesis example 56
The compound (compound) represented by the formula (I-57) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with acetonitrile (2-pyridylsulfonyl) while maintaining its molar ratio. 186) is obtained.

Synthesis example 57
The formula (I-58) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with N-octyl-((4-cyanoacetyl) phenyl) sulfonamide while maintaining its molar ratio. ) Is obtained (compound 164).

Synthesis example 58
The formula (I) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with N, N-dibutyl-((4-cyanoacetyl) phenyl) sulfonamide while maintaining its molar ratio. The compound represented by −59) (compound 160) is obtained.

Synthesis example 59
The formula (I-60) is the same as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate is replaced with N, N-diphenyl-((4-cyanoacetyl) phenyl) sulfonamide while maintaining its molar ratio. ) Is obtained (compound 161).

Synthesis example 60
Compound 0.513 represented by the formula (I-3) obtained in Synthesis Example 4 while stirring 7.6 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) at 3 ° C. Added a part. 3.8 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) was added to the obtained mixture. The resulting mixture was heated to 15 ° C. over 3 hours and 30 minutes with stirring. 139 parts of ice water was added to the obtained mixture, and 38.2 parts of sodium chloride was further added. The resulting mixture was filtered and the resulting residue was washed with 64 parts of a 21.5% aqueous sodium chloride solution. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 1.02 part of a compound represented by the formula (I-61) (a compound in which two sulfo groups were bonded to compound 102).

<Identification of the compound represented by the formula (I-61) (compound 102 to which two sulfo groups are bonded)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 560
Exact Mass: 561

Synthesis example 61
12.2 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 103 parts of methanol were mixed. While keeping the temperature at 4 to 6 ° C., a mixture of 14.3 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 130 parts of methanol was added to the obtained mixture over 2 hours and 10 minutes. And dropped. The resulting mixture was stirred at 4-6 ° C. for 6 hours. While keeping the temperature below 5 ° C., 9.37 parts of acetic acid and 13.8 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture. The resulting mixture was stirred at room temperature for 15 hours. To the obtained mixture, 1.00 part of acetic acid and 1.39 part of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at room temperature for 3 hours and at 40 ° C. for 2 hours and 30 minutes. To the obtained mixture, 1.44 parts of acetic acid and 2.13 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 40 ° C. for 3 hours. To the obtained mixture, 0.985 parts of acetic acid, 1.46 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 170 parts of methanol were added, and the mixture was stirred at 40 ° C. for 2 hours. To the obtained mixture, 9.29 parts of acetic acid, 12.2 parts of barbituric acid and 17 parts of methanol were added, and the mixture was stirred at 40 ° C. for 20 hours. To the obtained mixture, 9.29 parts of acetic acid, 14.4 parts of barbituric acid and 14 parts of methanol were added, and the mixture was stirred at 40 ° C. for 18 hours. The resulting mixture was filtered. The obtained residue was washed twice with a mixture of 200 parts of water and 200 parts of methanol, once with a mixture of 219 parts of water and 219 parts of methanol, and once with 500 parts of water. The obtained residue is dried under reduced pressure at 60 ° C. to obtain a mixture containing the compound represented by the formula (I-3) (Compound 102) and the compound represented by the formula (I-6) (Compound 466). I got 3 copies.

<Identification of compound represented by formula (I-3) (Compound 102)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 402
Exact Mass: 401
<Identification of compound represented by formula (I-6) (Compound 466)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 385
Exact Mass: 384

Synthesis example 62
11.5 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 136 parts of methanol were mixed. A mixture of 13.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 101 parts of methanol was added dropwise to the obtained mixture while keeping the temperature at 2 to 4 ° C. over 1 hour. did. The resulting mixture was stirred for 6 hours while keeping below 5 ° C. 8.88 parts of acetic acid, 3.2 parts of methanol and 16.3 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture while keeping the temperature at 4 to 8 ° C. The resulting mixture was stirred at room temperature for 16 hours. To the obtained mixture, 1.02 parts of acetic acid, 1.64 parts of 2-chlorobenzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol were added, and the mixture was added at room temperature for 1.5 hours and at 40 ° C. for 6 hours. Stirred. To the obtained mixture, 1.35 parts of acetic acid, 2.44 parts of 2-chlorobenzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol were added, and the mixture was stirred at 40 ° C. for 3 hours. To the obtained mixture, 1.16 parts of acetic acid, 2.03 parts of 2-chlorobenzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol were added, and the mixture was stirred at 40 ° C. for 17 hours. To the obtained mixture, 8.83 parts of acetic acid, 12.6 parts of barbituric acid and 14 parts of methanol were added, and the mixture was stirred at 40 ° C. for 22 hours. To the obtained mixture, 4.40 parts of acetic acid, 5.75 parts of barbituric acid and 14 parts of methanol were added, and the mixture was stirred at 40 ° C. for 9 hours and at room temperature for 4 hours. The resulting mixture was filtered. The obtained residue was washed once with 393 parts of methanol and once with a mixture of 393 parts of water and 393 parts of methanol. 800 parts of methanol was added to the obtained residue, and the mixture was stirred at 40 ° C. for 2 hours. The resulting mixture was filtered. The obtained residue is dried under reduced pressure at 40 ° C. to obtain 40 a mixture containing the compound represented by the formula (I-4) (Compound 112) and the compound represented by the formula (I-63) (Compound 476). I got 7 copies.

<Identification of compound represented by formula (I-4) (Compound 112)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469
<Identification of compound represented by formula (I-63) (Compound 476)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 419
Exact Mass: 418

Synthesis example 63
The compound (Compound 114) represented by the formula (I-5) and the formula (I) are the same as in Synthesis Example 62, except that 2-chlorobenzoylacetonitrile is replaced with 4-chlorobenzoylacetonitrile while maintaining its molar ratio. A mixture containing the compound represented by −64) (Compound 478) was obtained.

<Identification of compound represented by formula (I-5) (compound 114)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469
<Identification of compound represented by formula (I-64) (Compound 478)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 419
Exact Mass: 418

Synthesis example 64
The compound (Compound 101) represented by the formula (I-1) and the formula (I-) are represented in the same manner as in Synthesis Example 62, except that 2-chlorobenzoyl acetonitrile is replaced with pivaloyl acetonitrile while maintaining its molar ratio. A mixture containing the compound represented by 65) (Compound 465) was obtained.

<Identification of compound represented by formula (I-1) (Compound 101)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 362
Exact Mass: 361
<Identification of compound represented by formula (I-65) (Compound 465)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 365
Exact Mass: 364

Synthesis example 65
The compound (Compound 199) represented by the formula (I-66) and the formula (I-) were carried out in the same manner as in Synthesis Example 62 except that the phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio. A mixture containing the compound represented by 67) (Compound 563) was obtained.

<Identification of compound represented by formula (I-66) (Compound 199)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 515
Exact Mass: 514
<Identification of compound represented by formula (I-67) (Compound 563)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 464
Exact Mass: 463

Synthesis example 66
The formula (I) is the same as in Synthesis Example 62, except that phthalonitrile is replaced with 4-nitrophthalonitrile while maintaining its molar ratio, and 2-chlorobenzoylacetonitrile is replaced with 4-chlorobenzoylacetonitrile while maintaining its molar ratio. A mixture containing the compound represented by −68) (Compound 201) and the compound represented by the formula (I-69) (Compound 565) was obtained.

<Identification of compound represented by formula (I-68) (Compound 201)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 515
Exact Mass: 514
<Identification of compound represented by formula (I-69) (Compound 565)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 464
Exact Mass: 463

Synthesis example 67
The formula (Synthesis Example 62) was carried out in the same manner as in Synthesis Example 62, except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio and 2-chlorobenzoylacetonitrile was replaced with pivaloyl acetonitrile while maintaining its molar ratio. A mixture containing the compound represented by I-2) (Compound 188) and the compound represented by the formula (I-70) (Compound 552) was obtained.

<Identification of compound represented by formula (I-2) (Compound 188)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 407
Exact Mass: 406
<Identification of compound represented by formula (I-70) (Compound 552)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 410
Exact Mass: 409

Synthesis example 68
The formula (I-) was carried out in the same manner as in Synthesis Example 62, except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio and 2-chlorobenzoylacetonitrile was replaced with benzoylacetonitrile while maintaining its molar ratio. A mixture containing the compound represented by 35) (Compound 189) and the compound represented by the formula (I-72) (Compound 553) was obtained.

<Identification of compound (Compound 189) represented by formula (I-35)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 447
Exact Mass: 446
<Identification of compound represented by formula (I-72) (Compound 553)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 430
Exact Mass: 429

Synthesis example 69
The compound represented by the formula (I-4) (Compound 112) and the formula (I-73) are represented in the same manner as in Synthesis Example 62, except that the barbituric acid is replaced with benzoyl acetonitrile while maintaining its molar ratio. A mixture containing the compound (Compound 7) was obtained.

<Identification of compound represented by formula (I-4) (Compound 112)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469
<Identification of compound (Compound 7) represented by formula (I-73)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 436
Exact Mass: 435

Synthesis example 70
Formula (I-5) in the same manner as in Synthesis Example 62, except that 2-chlorobenzoylacetonitrile is replaced with 4-chloroacetonitrile while maintaining its molar ratio and barbituric acid is replaced with benzoylacetonitrile while maintaining its molar ratio. A mixture containing the compound represented by (Compound 114) and the compound represented by the formula (I-74) (Compound 8) was obtained.

<Identification of compound represented by formula (I-5) (compound 114)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469
<Identification of compound (Compound 8) represented by formula (I-74)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 436
Exact Mass: 435

Synthesis example 71
Represented by the formula (I-66) in the same manner as in Synthesis Example 62, except that phthalonitrile is replaced with 4-nitrophthalonitrile while maintaining its molar ratio and barbituric acid is replaced with benzoyl acetonitrile while maintaining its molar ratio. A mixture containing the compound (Compound 199) to be used and the compound (Compound 9) represented by the formula (I-75) was obtained.

<Identification of compound represented by formula (I-66) (Compound 199)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 515
Exact Mass: 514
<Identification of compound (Compound 9) represented by formula (I-75)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 481
Exact Mass: 480

Synthesis example 72
Replace phthalonitrile with 4-nitrophthalonitrile while preserving its molar ratio, replace 2-chlorobenzoylacetonitrile with 4-chlorobenzoylacetonitrile while preserving its molar ratio, and replace barbituric acid with benzoylacetonitrile while preserving its molar ratio. A mixture containing the compound represented by the formula (I-68) (Compound 201) and the compound represented by the formula (I-76) (Compound 10) was obtained in the same manner as in Synthesis Example 62 except for the substitution.

<Identification of compound represented by formula (I-68) (Compound 201)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 515
Exact Mass: 514
<Identification of compound (Compound 10) represented by formula (I-76)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 481
Exact Mass: 480

Synthesis example 73
The compound represented by the formula (I-3) (Compound 102) was carried out in the same manner as in Synthesis Example 61 except that the barbituric acid was replaced with dimedone (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining its molar ratio. ) And the compound represented by the formula (I-77) (Compound 454) were obtained.

<Identification of compound represented by formula (I-3) (Compound 102)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 402
Exact Mass: 401
<Identification of compound represented by formula (I-77) (Compound 454)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 397
Exact Mass: 396

Synthesis example 74
The same as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-oxo-3- (2-thienyl) propionitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The compound represented by the formula (I-78) (Compound 732) was obtained.

<Identification of compound represented by formula (I-78) (Compound 732)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 414
Exact Mass: 413

Synthesis example 75
In the same manner as in Synthesis Example 7, the formula (I-79) was used, except that methyl 4-cyanoacetylbenzoate was replaced with 2-floyl acetonitrile (manufactured by Sigma-Aldrich Japan Co., Ltd.) while maintaining its molar ratio. The represented compound (Compound 733) was obtained.

<Identification of compound represented by formula (I-79) (Compound 733)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 382
Exact Mass: 381

Synthesis example 76
The compound (Compound 135) represented by the formula (I-44) and the formula (I) are the same as in Synthesis Example 62, except that 2-chlorobenzoylacetonitrile is replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by -80) (Compound 499) was obtained.

<Identification of compound represented by formula (I-44) (Compound 135)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489
<Identification of compound represented by formula (I-80) (Compound 499)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 427
Exact Mass: 428

Synthesis example 77
The compound (Compound 136) represented by the formula (I-45) and the formula (I) are the same as in Synthesis Example 62, except that 2-chlorobenzoylacetonitrile is replaced with 4-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by −81) (Compound 500) was obtained.

<Identification of compound represented by formula (I-45) (Compound 136)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489
<Identification of compound (Compound 500) represented by formula (I-81)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 427
Exact Mass: 428

Synthesis example 78
The formula (similar to Synthesis Example 62) was used, except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio, and 2-chlorobenzoyl acetonitrile was replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by I-82) (Compound 222) and the compound represented by the formula (I-83) (Compound 586) was obtained.

<Identification of compound represented by formula (I-82) (Compound 222)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 533
Exact Mass: 534
<Identification of compound represented by formula (I-83) (Compound 586)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 472
Exact Mass: 473

Synthesis example 79
The formula (similar to Synthesis Example 62) was used, except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio, and 2-chlorobenzoyl acetonitrile was replaced with 4-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by I-84) (Compound 223) and the compound represented by the formula (I-85) (Compound 587) was obtained.

<Identification of compound represented by formula (I-84) (Compound 223)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 533
Exact Mass: 534
<Identification of compound represented by formula (I-85) (Compound 587)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 472
Exact Mass: 473

Synthesis example 80
The compound (Compound 134) represented by the formula (I-43) and the formula (I) are the same as in Synthesis Example 62, except that 2-chlorobenzoylacetonitrile is replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by −86) (Compound 498) was obtained.

<Identification of compound (Compound 134) represented by formula (I-43)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 488
Exact Mass: 489
<Identification of compound represented by formula (I-86) (Compound 498)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 427
Exact Mass: 428

Synthesis example 81
The formula (similar to Synthesis Example 62) was used, except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio, and 2-chlorobenzoyl acetonitrile was replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio. A mixture containing the compound represented by I-87) (Compound 221) and the compound represented by the formula (I-88) (Compound 585) was obtained.

<Identification of compound (Compound 221) represented by formula (I-87)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 533
Exact Mass: 534
<Identification of compound (Compound 585) represented by formula (I-88)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 472
Exact Mass: 473

Raw material synthesis example 1
At −78 ° C., acetonitrile has four times the number of moles of 10 parts of methyl 4- (carboxymethyl) benzoate, and lithium has 3 times the number of moles of 10 parts of methyl 4- (carboxymethyl) benzoate. A mixture of bis (trimethylsilyl) amide and 130 parts of tetrahydrofuran was obtained. A mixture of 10 parts of methyl 4- (carboxymethyl) benzoate and 90 parts of tetrahydrofuran was added to this mixture, and the mixture was stirred at −78 ° C. to room temperature for 16 hours. The resulting mixture was purified to give 8 parts of 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 202
Exact Mass: 203

Raw material synthesis example 2
At −78 ° C., acetonitrile has 6 times the number of moles of 33 parts of methyl 4- (2-carboxyethyl) benzoate, and 5.5 has the number of moles of 33 parts of methyl 4- (2-carboxyethyl) benzoate. A mixture of 280 parts of lithium bis (trimethylsilyl) amide and tetrahydrofuran was obtained in double the number of moles. To this mixture, 33 parts of methyl 4- (2-carboxyethyl) benzoate was added, and the mixture was stirred at −78 ° C. for 30 minutes. The resulting mixture was purified to give 29 parts of 4- (2-carboxyethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 4- (2-carboxyethyl) -1- (cyanomethylcarbonyl) benzene>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 216
Exact Mass: 217

Raw material synthesis example 3
At −78 ° C., acetonitrile has four times the number of moles of 30 parts of methyl 2- (carboxymethyl) benzoate, and lithium has three times the number of moles of methyl 2- (carboxymethyl) benzoate. A mixture of bis (trimethylsilyl) amide and 270 parts of tetrahydrofuran was obtained. A mixture of 30 parts of methyl 2- (carboxymethyl) benzoate and 270 parts of tetrahydrofuran was added to this mixture, and the mixture was stirred at −78 ° C. to room temperature for 3 hours. The resulting mixture was purified to give 27 parts of 2- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 2- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 202
Exact Mass: 203

Raw material synthesis example 4
At −78 ° C., the number of moles of acetonitrile is 6 times the number of moles of 34 parts of 4- (2- (methoxycarbonyl) ethyl) benzoic acid, and the number of moles of 34 parts of 4- (2- (methoxycarbonyl) ethyl) benzoic acid. A mixture of lithium bis (trimethylsilyl) amide and 1200 parts of tetrahydrofuran was obtained in 5.5 times the number of moles of the above. To this mixture, 34 parts of 4- (2- (methoxycarbonyl) ethyl) benzoic acid was added, and the mixture was stirred at −78 ° C. for 1 hour. The obtained mixture was purified by recrystallization using ethyl acetate and hexane to obtain 30 parts of 4- (2- (cyanomethylcarbonyl) ethyl) benzoic acid.

<Identification of 4- (2- (cyanomethylcarbonyl) ethyl) benzoic acid>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 216
Exact Mass: 217

Raw material synthesis example 5
At −78 ° C., the number of moles of acetonitrile is 5.5 times the number of moles of 28 parts of 4- (methoxycarbonylmethyl) benzoic acid, and the number of moles is 5 times the number of moles of 28 parts of 4- (methoxycarbonylmethyl) benzoic acid. A mixture of n-butyllithium and 1100 parts of tetrahydrofuran was obtained. To this mixture, 28 parts of 4- (methoxycarbonylmethyl) benzoic acid was added, and the mixture was stirred at −78 ° C. for 15 minutes. The resulting mixture was purified by column chromatography to give 22 parts of 4- (cyanomethylcarbonylmethyl) benzoic acid.

<Identification of 4- (cyanomethylcarbonylmethyl) benzoic acid>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 202
Exact Mass: 203

Raw material synthesis example 6
At −78 ° C., acetonitrile has four times the number of moles of 18 parts of 4- (methoxycarbonyl) -3-methoxybenzoic acid, and 3 of the number of moles of 18 parts of 4- (methoxycarbonyl) -3-methoxybenzoic acid. A mixture of double the number of moles of lithium bis (trimethylsilyl) amide and 160 parts of tetrahydrofuran was obtained. A mixture of 18 parts of 4- (methoxycarbonyl) -3-methoxybenzoic acid and 160 parts of tetrahydrofuran was added to this mixture, and the mixture was stirred at −78 ° C. to room temperature for 16 hours. The resulting mixture was purified to give 15 parts of 4- (cyanomethylcarbonyl) -3-methoxybenzoic acid.

<Identification of 4- (cyanomethylcarbonyl) -3-methoxybenzoic acid>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 218
Exact Mass: 219

Raw material synthesis example 7
At −78 ° C., the number of moles of acetonitrile is four times the number of moles of 14 parts of 4- (methoxycarbonyl) -2-methoxybenzoic acid, and the number of moles of 14 parts of 4- (methoxycarbonyl) -2-methoxybenzoic acid is 3 A mixture of double the number of moles of lithium bis (trimethylsilyl) amide and 120 parts of tetrahydrofuran was obtained. A mixture of 14 parts of 4- (methoxycarbonyl) -2-methoxybenzoic acid and 120 parts of tetrahydrofuran was added to this mixture, and the mixture was stirred at −78 ° C. to room temperature for 16 hours. The resulting mixture was purified to give 13 parts of 4- (cyanomethylcarbonyl) -2-methoxybenzoic acid.

<Identification of 4- (cyanomethylcarbonyl) -2-methoxybenzoic acid>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 218
Exact Mass: 219

Synthesis example 82
5 parts of 4-aminophthalonitrile and 40 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in 0.5 times the number of moles of 5 parts of 4-aminophthalonitrile was added to the obtained mixture while keeping the temperature below 5 ° C. The mixture was stirred at 5 ° C. for 3 hours and at room temperature for 16 hours. To the obtained mixture, benzoyl acetonitrile having a molar number of 2.2 times the molar number of 5 parts of 4-aminophthalonitrile and 5.3 parts of acetic acid were added. The mixture was stirred at room temperature for 32 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound represented by the formula (I-89) (Compound 21-55). ..

<Identification of compound represented by formula (I-89) (Compound 21-55)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 417
Exact Mass: 416

Synthesis example 83
5 parts of 4- (N-acetylamino) phthalonitrile and 40 parts of methanol were mixed. Keeping the temperature below 5 ° C., a 25% sodium methoxide methanol solution containing sodium methoxide having a molar number of 0.5 times the molar number of 5 parts of 4- (N-acetylamino) phthalonitrile was added to the obtained mixture. added. The mixture was stirred at 5 ° C. for 3 hours and at room temperature for 16 hours. To the obtained mixture, benzoyl acetonitrile having a molar number of 2.2 times the molar number of 5 parts of 4- (N-acetylamino) phthalonitrile and 5.3 parts of acetic acid were added. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.2 part of the compound represented by the formula (I-90) (Compound 21-185). ..

<Identification of compound represented by formula (I-90) (Compound 21-185)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [MH] ⁺ 459
Exact Mass: 458

Synthesis example 84
3 parts of 4-carboxyphthalonitrile and 32 parts of ethanol were mixed. To the resulting mixture was added a 21% sodium ethoxide ethanol solution containing sodium ethoxide in 2.1 times the number of moles of 3 parts of 4-carboxyphthalonitrile at room temperature. The mixture was stirred at 60 ° C. for 16 hours. To the obtained mixture, benzoyl acetonitrile having a mole number of 2.3 times the number of moles of 3 parts of 4-carboxyphthalonitrile and 9.4 parts of acetic acid were added. The mixture was stirred at 90 ° C. for 20 hours. 9.4 parts of acetic acid was added to the resulting mixture. The mixture was stirred at 90 ° C. for 72 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.5 part of the compound represented by the formula (I-91) (Compound 21-135). ..

<Identification of compound represented by formula (I-91) (Compound 21-135)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 444
Exact Mass: 445

Synthesis example 85
3 parts of 4-carboxyphthalonitrile and 47 parts of ethanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in the number of moles twice the number of moles of 3 parts of 4-carboxyphthalonitrile at room temperature. The mixture was stirred at 60 ° C. for 16 hours. To the obtained mixture, 9.4 parts of acetic acid and 120 parts of 4-cyanoacetylbenzoic acid and 120 parts of methanol were added in 2.3 times the number of moles of 3 parts of 4-carboxyphthalonitrile. The mixture was stirred at 70 ° C. for 96 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.2 part of the compound represented by the formula (I-92) (Compound 21-144). ..

<Identification of compound represented by formula (I-92) (Compound 21-144)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 532
Exact Mass: 533

Synthesis example 86
3 parts of 4,5-dichlorophthalonitrile and 48 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing 1 times the number of moles of sodium methoxide in 3 parts of 4,5-dichlorophthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at room temperature for 16 hours. To the obtained mixture was added 6.3 parts of acetic acid, and 160 parts of 4-cyanoacetylbenzoic acid and methanol having 2.2 times the number of moles of 4,5-dichlorophthalonitrile. The mixture was stirred at room temperature for 48 hours and at 50 ° C. for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.6 part of the compound represented by the formula (I-93) (Compound 21-40). ..

<Identification of compound represented by formula (I-93) (Compound 21-40)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 556
Exact Mass: 557

Synthesis example 87
5 parts of 4-methoxyphthalonitrile and 79 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide having a molar number 2.5 times the molar number of 5 parts of 4-methoxyphthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at room temperature for 3 hours and at 65 ° C. for 3 hours. To the obtained mixture was added 4-cyanoacetylbenzoic acid, 160 parts of methanol and 21 parts of acetic acid, which had 2.2 times the number of moles of 5 parts of 4-methoxyphthalonitrile. The mixture was stirred at room temperature for 64 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.6 part of the compound represented by the formula (I-94) (Compound 21-169). ..

<Identification of compound represented by formula (I-94) (Compound 21-169)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 518
Exact Mass: 519

Synthesis example 88
5 parts of 4-methoxyphthalonitrile and 79 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing twice the number of moles of sodium methoxide as the number of moles of 5 parts of 4-methoxyphthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at 70 ° C. for 5 hours. To the obtained mixture was added 3-cyanoacetylbenzoic acid, 160 parts of methanol and 21 parts of acetic acid, which had 2.5 times the number of moles of 5 parts of 4-methoxyphthalonitrile. The mixture was stirred at room temperature for 68 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.6 part of the compound represented by the formula (I-95) (Compound 21-168). ..

<Identification of compound represented by formula (I-95) (Compound 21-168)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 518
Exact Mass: 519

Synthesis example 89
8 parts of 4-methoxyphthalonitrile and 95 parts of methanol were mixed. At room temperature, a 25% sodium methoxide methanol solution containing sodium methoxide having a molar number 2.5 times the molar number of 8 parts of 4-methoxyphthalonitrile was added to the obtained mixture. The mixture was stirred at 65 ° C. for 3 hours. To the obtained mixture was added 2-cyanoacetylbenzoic acid and 34 parts of acetic acid, which had 2.2 times the number of moles of 8 parts of 4-methoxyphthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.4 part of the compound represented by the formula (I-96) (Compound 21-167). ..

<Identification of compound represented by formula (I-96) (Compound 21-167)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 518
Exact Mass: 519

Synthesis example 90
2 parts of 4-carboxyphthalonitrile and 32 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing twice the number of moles of sodium methoxide as the number of moles of 2 parts of 4-carboxyphthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at 60 ° C. for 6 hours. In the obtained mixture, 4.2 parts of acetic acid, 2 parts of 4-carboxyphthalonitrile, and 95 parts of 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene and methanol having 2.2 times the number of moles. Was added. The mixture was stirred at 70 ° C. for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound represented by the formula (I-97) (Compound 22-4961). ..

<Identification of the compound represented by the formula (I-97) (Compound 22-4961)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 560
Exact Mass: 561

Synthesis example 91
6.51 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 58 parts of methanol were mixed. A mixture of 7.61 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 71 parts of methanol was added dropwise to the obtained mixture over 1 hour and 30 minutes while keeping the temperature below 5 ° C. .. The resulting mixture was stirred at 5 ° C. or lower for 12 hours. While keeping the temperature below 5 ° C., 15.0 parts of acetic acid was added to the obtained mixture, and 30.2 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 927 parts of methanol were added. The obtained mixture was stirred at room temperature for 4 hours and then at 40 ° C. for 96 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.882 parts of the compound (Compound 112) represented by the formula (I-4).

<Identification of compound represented by formula (I-4) (Compound 112)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 470
Exact Mass: 469

Synthesis example 92
5.44 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 64 parts of methanol were mixed. A mixture of 6.37 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 48 parts of methanol was added dropwise to the obtained mixture at 5 ° C. or lower over 1 hour and 30 minutes. did. The resulting mixture was stirred for 12 hours while keeping below 5 ° C. While keeping the temperature below 5 ° C., 4.20 parts of acetic acid, 742 parts of methanol and 7.69 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture. The resulting mixture was stirred at room temperature for 36 hours. To the obtained mixture, 0.482 parts of acetic acid and 0.775 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at room temperature for 3 hours and at 40 ° C. for 12 hours. To the obtained mixture, 0.638 parts of acetic acid and 1.15 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 40 ° C. for 6 hours. To the obtained mixture, 0.549 parts of acetic acid and 0.958 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 40 ° C. for 36 hours. 4.17 parts of acetic acid and 5.96 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 ° C. for 48 hours. 2.08 parts of acetic acid and 2.72 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 ° C. for 24 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.283 parts of a compound (Compound 476) represented by the formula (I-63).

<Identification of compound represented by formula (I-63) (Compound 476)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 419
Exact Mass: 418

Synthesis example 93
7.51 parts of 4,5-dichlorophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 130 parts of methanol were mixed. While keeping the temperature at 0 ° C., 7.41 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture over 1 hour and 30 minutes. The resulting mixture was stirred at room temperature for 16 hours. At room temperature, 16.0 parts of acetic acid, 670 parts of methanol and 7.27 parts of 4-cyanoacetylbenzoic acid were added to the obtained mixture. The resulting mixture was stirred at room temperature for 12 hours and at 50 ° C. for 12 hours. To the obtained mixture, 0.433 parts of acetic acid and 0.733 parts of 4-cyanoacetylbenzoic acid were added, and the mixture was stirred at 50 ° C. for 6 hours. To the obtained mixture, 0.573 parts of acetic acid and 1.09 parts of 4-cyanoacetylbenzoic acid were added, and the mixture was stirred at 50 ° C. for 6 hours. To the obtained mixture, 0.493 parts of acetic acid and 0.906 parts of 4-cyanoacetylbenzoic acid were added, and the mixture was stirred at 50 ° C. for 12 hours. 3.75 parts of acetic acid and 5.35 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 50 ° C. for 24 hours. 1.87 parts of acetic acid and 2.44 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 50 ° C. for 24 hours. The obtained mixture was distilled off with a rotary evaporator, and then the obtained residue was purified by column chromatography to obtain 0.252 parts of the compound represented by the formula (I-98) (Compound 31-40). rice field.

<Identification of compound represented by formula (I-98) (Compound 31-40)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 495
Exact Mass: 496

Synthesis example 94
The formula (I-) was the same as in Synthesis Example 92, except that 2-chlorobenzoylacetonitrile was replaced with 4-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid was replaced with benzoylacetonitrile while maintaining its molar ratio. A compound represented by 99) (Compound 01-10) was obtained.

<Identification of compound represented by formula (I-99) (Compound 01-10)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 444
Exact Mass: 445

Synthesis example 95
Phtalonitrile is replaced with 4-nitrophthalonitrile while maintaining its molar ratio, 2-chlorobenzoylacetonitrile is replaced with 4-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid is replaced with benzoylacetonitrile while maintaining its molar ratio. A compound represented by the formula (I-100) (Compound 01-364) was obtained in the same manner as in Synthesis Example 92 except that the compound (I-100) was obtained.

<Identification of compound represented by formula (I-100) (Compound 01-364)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 489
Exact Mass: 490

Synthesis example 96
A compound represented by the formula (I-101) (Compound 01-124) was obtained in the same manner as in Synthesis Example 93 except that barbituric acid was replaced with benzoyl acetonitrile while maintaining its molar ratio.

<Identification of compound represented by formula (I-101) (Compound 01-124)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 512
Exact Mass: 513

Synthesis example 97
The formula (I-) was the same as in Synthesis Example 92, except that 2-chlorobenzoylacetonitrile was replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid was replaced with benzoylacetonitrile while maintaining its molar ratio. The compound represented by 102) (Compound 01-37) was obtained.

<Identification of compound represented by formula (I-102) (Compound 01-37)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 444
Exact Mass: 445

Synthesis example 98
Phtalonitrile is replaced with 4-nitrophthalonitrile while maintaining its molar ratio, 2-chlorobenzoylacetonitrile is replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid is replaced with benzoylacetonitrile while maintaining its molar ratio. The compound represented by the formula (I-103) (Compound 01-391) was obtained in the same manner as in Synthesis Example 92 except that the compound was replaced with the above.

<Identification of compound represented by formula (I-103) (Compound 01-391)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 489
Exact Mass: 490

Synthesis example 99
The formula (I) was the same as in Synthesis Example 93, except that 4-cyanoacetylbenzoic acid was replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid was replaced with benzoylacetonitrile while maintaining its molar ratio. A compound represented by −104) (Compound 01-151) was obtained.

<Identification of compound represented by formula (I-104) (Compound 01-151)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 512
Exact Mass: 513

Synthesis example 100
3 parts of 4-bromophthalonitrile and 24 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in 0.5 times the number of moles of 3 parts of 4-bromophthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at 0 ° C. for 3 hours. To the resulting mixture was added 3.1 parts of 4-cyanoacetylbenzoic acid and acetic acid, which had 2.2 times the number of moles of 3 parts of 4-bromophthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound represented by the formula (I-105) (Compound 21-294). ..

<Identification of compound represented by formula (I-105) (Compound 21-294)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 566
Exact Mass: 567

Synthesis example 101
5 parts of 3,4-dicyanobenzenesulfonic acid and 79 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing 0.5 times the number of moles of 3,4-dicyanobenzenesulfonic acid in 5 parts of sodium methoxide was added to the obtained mixture while keeping the temperature at 0 ° C. The mixture was stirred at 0 ° C. for 6 hours. To the resulting mixture was added 4.2 parts of 4-cyanoacetylbenzoic acid and 5.2 parts of acetic acid, which had 2.2 times the number of moles of 5 parts of 3,4-dicyanobenzenesulfonic acid. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.4 part of the compound represented by the formula (I-106) (Compound 21-219). ..

<Identification of compound represented by formula (I-106) (Compound 21-219)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 568
Exact Mass: 569

Synthesis example 102
2 parts of phthalonitrile and 16 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in 0.5 times the number of moles of 2 parts of phthalonitrile was added to the obtained mixture while keeping the temperature at 5 ° C. The mixture was stirred at 5 ° C. for 3 hours. To the resulting mixture was added 2.2 parts of N-acetyl-4- (cyanoacetyl) aniline and 2.2 parts of acetic acid, which had 2.2 times the number of moles of 2 parts of phthalonitrile. The mixture was stirred at room temperature for 16 hours. To the obtained mixture, N-acetyl-4- (cyanoacetyl) aniline having a molar number 1.1 times the number of moles of 2 parts of phthalonitrile was added. The mixture was stirred at room temperature for 16 hours and at 50 ° C. for 48 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound (Compound 154) represented by the formula (I-107).

<Identification of compound (Compound 154) represented by formula (I-107)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 516
Exact Mass: 515

Synthesis example 103
Two parts of 4- (trifluoromethyl) phthalonitrile and 32 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing 0.8 times the number of moles of sodium methoxide as the number of moles of 2 parts of 4- (trifluoromethyl) phthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. .. The mixture was stirred at 10 ° C. for 2 hours. To the resulting mixture was added 4-cyanoacetylbenzoic acid, which has 2.2 times the number of moles of 4.4 parts of acetic acid and 2 parts of 4- (trifluoromethyl) phthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound represented by the formula (I-108) (Compound 21-119). ..

<Identification of compound represented by formula (I-108) (Compound 21-119)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 556
Exact Mass: 557

Synthesis example 104
4 parts of 4- (trifluoromethyl) phthalonitrile and 32 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in 0.5 times the number of moles of 4 parts of 4- (trifluoromethyl) phthalonitrile was added to the obtained mixture while keeping the temperature at 0 ° C. .. The mixture was stirred at 0 ° C. for 3 hours. To the resulting mixture was added 4.4 parts of 3-cyanoacetylbenzoic acid and acetic acid in 2.2 times the number of moles of 4 parts of 4- (trifluoromethyl) phthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound represented by the formula (I-109) (Compound 21-118). ..

<Identification of compound represented by formula (I-109) (Compound 21-118)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 556
Exact Mass: 557

Synthesis example 105
2.5 parts of 4- (trifluoromethyl) phthalonitrile and 79 parts of methanol were mixed. While keeping the temperature at 0 ° C., a 25% sodium methoxide methanol solution containing 2.5 times the number of moles of sodium methoxide in 2.5 parts of 4- (trifluoromethyl) phthalonitrile was added to the obtained mixture. added. The mixture was stirred at 0 ° C. for 3 hours. To the resulting mixture was added 2-cyanoacetylbenzoic acid and 3 parts acetic acid in 2.2 times the number of moles of 2.5 parts of 4- (trifluoromethyl) phthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.1 part of the compound represented by the formula (I-110) (Compound 21-117). ..

<Identification of compound represented by formula (I-110) (Compound 21-117)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 556
Exact Mass: 557

Synthesis example 106
2 parts of phthalonitrile and 16 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in 0.5 times the number of moles of 2 parts of phthalonitrile was added to the obtained mixture while keeping the temperature at 5 ° C. The mixture was stirred at 5 ° C. for 3 hours and at room temperature for 16 hours. To the resulting mixture was added 2.2 parts of 4-sulfamoylbenzoyl acetonitrile and 2.2 parts of acetic acid, which had 2.2 times the number of moles of 2 parts of phthalonitrile. The mixture was stirred at room temperature for 16 hours. After distilling off the solvent of the obtained mixture with a rotary evaporator, the obtained residue was purified by column chromatography to obtain 0.3 part of the compound (Compound 157) represented by the formula (I-42).

<Identification of compound represented by formula (I-42) (Compound 157)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 560
Exact Mass: 559

Synthesis example 107
4.1 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 48 parts of methanol were mixed. A mixture of 4.8 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 36 parts of methanol was added dropwise to the obtained mixture at 5 ° C. or lower over 1 hour and 30 minutes. did. The resulting mixture was stirred for 12 hours while keeping below 5 ° C. 5.1 parts of acetic acid, 750 parts of methanol and 7.2 parts of 4-sulfamoylbenzoylacetonitrile were added to the obtained mixture while keeping the temperature below 5 ° C. The resulting mixture was stirred at room temperature for 36 hours. To the obtained mixture, 0.56 part of acetic acid and 0.73 part of 4-sulfamoylbenzoylacetonitrile were added, and the mixture was stirred at room temperature for 3 hours and at 40 ° C. for 12 hours. 0.77 parts of acetic acid and 1.1 parts of 4-sulfamoylbenzoyl acetonitrile were added to the obtained mixture, and the mixture was stirred at 40 ° C. for 6 hours. To the obtained mixture, 0.66 parts of acetic acid and 0.90 parts of 4-sulfamoylbenzoylacetonitrile were added, and the mixture was stirred at 40 ° C. for 36 hours. 3.1 parts of acetic acid and 4.5 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 ° C. for 48 hours. 1.6 parts of acetic acid and 2.0 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 ° C. for 24 hours. The obtained mixture was distilled off with a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.21 part of a compound (Compound 521) represented by the formula (I-111).

<Identification of compound (Compound 521) represented by formula (I-111)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 464
Exact Mass: 463

Synthesis example 108
A compound (Compound 608) represented by the formula (I-112) was obtained in the same manner as in Synthesis Example 107 except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio.

<Identification of compound (Compound 608) represented by formula (I-112)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 509
Exact Mass: 508

Synthesis example 109
A compound (Compound 241) represented by the formula (I-113) was obtained in the same manner as in Synthesis Example 102 except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio.

<Identification of compound (Compound 241) represented by formula (I-113)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 561
Exact Mass: 560

Synthesis example 110
A compound (Compound 244) represented by the formula (I-114) was obtained in the same manner as in Synthesis Example 106 except that phthalonitrile was replaced with 4-nitrophthalonitrile while maintaining its molar ratio.

<Identification of compound (Compound 244) represented by formula (I-114)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 605
Exact Mass: 604

Synthesis example 111
The compound represented by the formula (I-115) (Compound 21-292) was prepared in the same manner as in Synthesis Example 100 except that 4-cyanoacetylbenzoic acid was replaced with 2-cyanoacetylbenzoic acid while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-115) (Compound 21-292)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 566
Exact Mass: 567

Synthesis example 112
The compound represented by the formula (I-116) (Compound 21-293) was prepared in the same manner as in Synthesis Example 100 except that 4-cyanoacetylbenzoic acid was replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio. Obtained.

<Identification of compound represented by formula (I-116) (Compound 21-293)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 566
Exact Mass: 567

Synthesis example 113
The compound represented by the formula (I-117) (Compound 41) was carried out in the same manner as in Synthesis Example 93 except that the barbituric acid was replaced with dimedone (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining its molar ratio. -843) was obtained.

<Identification of compound represented by formula (I-117) (Compound 41-843)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 507
Exact Mass: 508

Synthesis Example 114-Synthesis Example 165
Phthalonitrile is replaced with the compound represented by the formula (PPA-1) using the groups shown in the "B ¹ B ² " column of Table 12, and 2-chlorobenzoyl acetonitrile is used in the "Lk" column and "Hd" of Table 12. The compound shown in the “Compound” column of Table 12 was obtained by carrying out the same procedure as in Synthesis Example 91 except that the group represented by the formula (PPA-2) was used in place of the compound represented by the formula (PPA-2).
The compound obtained in each synthetic example is a compound represented by the ^{formula (PPA-3) using the groups shown in the "B 1} B ² " column, the "Lk" column and the "Hd" column of Table 12.
Compound identification was performed by mass spectrometry.
When the "ionization mode" column of Table 12 is "1", the value detected by (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ is shown in the "detection value" column of Table 12. ..
If "ionization mode" column of Table 12 is "-1", (Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - the detected values, "detection values in Table 12 Shown in the column.
In the "Exact. Mass." Column of Table 12, Exact. Mass. Indicates the value of.
In Table 12, ^{the symbols (HH35, BB19, etc.) described in the “B 1} B ² ” column and the “Hd” column are the same as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification. Defined in.

Synthesis Example 166 to Synthesis Example 181
The procedure was carried out in the same manner as in Synthesis Example 86, except that 4-cyanoacetylbenzoic acid was replaced with the compound represented by the formula (PPA-2) using the groups shown in the “Lk” and “Hd” columns of Table 13. , The compounds shown in the "Compound" column of Table 13 were obtained.
The compound obtained in each synthesis example is a compound represented by the formula (I-93a) using the groups shown in the "Lk" column and the "Hd" column of Table 13.
Compound identification was performed by mass spectrometry.
When the "ionization mode" column of Table 13 is "1", the values detected by (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ are shown in the "detection value" column of Table 13. ..
If "ionization mode" column of Table 13 is "-1", (Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - the detected values, "detection values in Table 13 Shown in the column.
In the "Exact. Mass." Column of Table 13, Exact. Mass. Indicates the value of.
In Table 13, the symbols (HH35, etc.) described in the “Hd” column are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

Synthesis example 182 to 223
Phthalonitrile is replaced with the compound represented by the formula (PPA-1) using the groups shown in the "B ¹ B ² " column of Table 14, and 2-chlorobenzoyl acetonitrile is replaced with the "Lk" column and "Hd" of Table 14. The compound shown in the "Compound" column of Table 14 was obtained by carrying out the same procedure as in Synthesis Example 92 except that the group represented by the formula (PPA-2) was used in place of the compound represented by the formula (PPA-2).
The compound obtained in each synthetic example is a compound represented ^{by the formula (I-63a) using the groups shown in the "B 1} B ² " column, the "Lk" column and the "Hd" column of Table 14.
Compound identification was performed by mass spectrometry.
When the "ionization mode" column of Table 14 is "1", the values detected by (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ are shown in the "detection value" column of Table 14. ..
If "ionization mode" column of Table 14 is "-1", (Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - the detected values, "detection values in Table 14 Shown in the column.
In the "Exact. Mass." Column of Table 14, Exact. Mass. Indicates the value of.
In Table 14, ^{the symbols described in the “B 1} B ² ” column and the “Hd” column are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

Synthesis Example 224 to Synthesis Example 237
The procedure was carried out in the same manner as in Synthesis Example 93, except that 4-cyanoacetylbenzoic acid was replaced with the compound represented by the formula (PPA-2) using the groups shown in the “Lk” and “Hd” columns of Table 15. , The compounds shown in the "Compounds" column of Table 15 were obtained.
The compound obtained in each synthesis example is a compound represented by the formula (I-98a) using the groups shown in the "Lk" column and the "Hd" column of Table 15.
Compound identification was performed by mass spectrometry.
When the "ionization mode" column of Table 15 is "1", the values detected by (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ are shown in the "detection value" column of Table 15. ..
If "ionization mode" column of Table 15 is "-1", (Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - the detected values, "detection values in Table 15 Shown in the column.
In the "Exact. Mass." Column of Table 15, Exact. Mass. Indicates the value of.
In Table 15, the symbols described in the “Hd” column are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

Synthesis Example 238 to Synthesis Example 240
Phthalonitrile is replaced with the compound represented by the formula (PPA-1) using the groups shown in the "B ¹ B ² " column of Table 16, and 2-chlorobenzoyl acetonitrile is replaced with the "Lk" column and "Hd" of Table 16. In the same manner as in Synthesis Example 92, except that the compound represented by the formula (PPA-2) is replaced with the compound represented by the formula (PPA-2) and the barbituric acid is replaced with dimedone, the same procedure as in Synthesis Example 92 is carried out, and the “Compound” column in Table 16 is used. The compound shown is obtained.
The compound obtained in each synthetic example is a compound represented ^{by the formula (I-63b) using the groups shown in the "B 1} B ² " column, the "Lk" column and the "Hd" column of Table 16.
Compound identification was performed by mass spectrometry.
When the "ionization mode" column of Table 16 is "1", the values detected by (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ are shown in the "detection value" column of Table 16. ..
If "ionization mode" column of Table 16 is "-1", (Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - the detected values, "detection values in Table 16 Shown in the column.
In the "Exact. Mass." Column of Table 16, Exact. Mass. Indicates the value of.
In Table 16, ^{the symbols described in the “B 1} B ² ” column and the “Hd” column are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

Synthesis example 241
The formula (I-) was the same as in Synthesis Example 92, except that 2-chlorobenzoylacetonitrile was replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid was replaced with benzoylacetonitrile while maintaining its molar ratio. The compound represented by 118) (Compound 01-24) was obtained.

<Identification of compound represented by formula (I-118) (Compound 01-24)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 444
Exact Mass: 445

Synthesis example 242
Phtalonitrile is replaced with 4-nitrophthalonitrile while maintaining its molar ratio, 2-chlorobenzoylacetonitrile is replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid is replaced with benzoylacetonitrile while maintaining its molar ratio. The compound represented by the formula (I-119) (Compound 01-378) was obtained in the same manner as in Synthesis Example 92 except that the compound was replaced with the above.

<Identification of the compound represented by the formula (I-119) (Compound 01-378)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 489
Exact Mass: 490

Synthesis example 243
The formula (I) is the same as in Synthesis Example 93, except that 4-cyanoacetylbenzoic acid is replaced with 3-cyanoacetylbenzoic acid while maintaining its molar ratio, and barbituric acid is replaced with benzoylacetonitrile while maintaining its molar ratio. A compound represented by −120) (Compound 01-138) was obtained.

<Identification of compound represented by formula (I-120) (Compound 01-138)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 512
Exact Mass: 513

Resin synthesis example 1
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Then 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.2.10 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decane-9-ylacrylate and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a mixed solution prepared by dissolving 33 parts of 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) having a solid content of 35.0%. The weight average molecular weight of the obtained resin B1 was 8800, the dispersity was 2.1, and the solution acid value was 28 mg-KOH / g.

Resin synthesis example 2
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 350 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85 ° C. with stirring. Then 70 parts acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and / or 3,4-epoxytricyclo [5.2.1.0]. ^2,6 ] A mixed solution of 202 parts of a mixture of decane-9-ylacrylate, 78 parts of vinyl toluene (isomer mixture) and 100 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 33 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropping of the initiator solution was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B5) having a solid content of 38.1%. The obtained resin B5 had a weight average molecular weight of 10400, a dispersity of 2.03, and a solution acid value of 53 mg-KOH / g.

Resin synthesis example 3
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 362 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Then 58 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and / or 3,4-epoxytricyclo [5.2.1.0]. ^2,6 ] A mixed solution of 167 parts of a mixture of decane-9-ylacrylate, 65 parts of 2-ethylhexyl acrylate and 111 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 27 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 210 parts of propylene glycol monomethyl ether acetate was added dropwise over 5.5 hours. After the dropping of the initiator solution was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B6) having a solid content of 29.8%. The obtained resin B6 had a weight average molecular weight of 10900, a dispersity of 2.25, and a solution acid value of 44 mg-KOH / g.

Comparative Example 1
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Pigment: C.I. I. Pigment Yellow 138 22 copies,
Dispersant 7.1 parts,
9.3 parts of the resin and 140 parts of the solvent (E): propylene glycol monomethyl ether acetate were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion liquid.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of pigment dispersion obtained;
Resin (B): 48 parts of resin B6 solution;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
11 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.7 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; manufactured by BASF) 4.5 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.57 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 330 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a comparative color curable composition 1.

[Creation of coloring pattern]
The comparative color-curable composition 1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a color-curable composition layer. .. After cooling, the distance between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used under an air atmosphere of 80 mJ / Exposure was performed with an exposure amount of cm ^{2 (based on 365 nm).} As the photomask, a photomask having a line-and-space pattern of 100 μm was used. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 70 seconds to develop and washed with water. This colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a colored pattern.
The film thickness of the obtained coloring pattern was measured using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.). The film thickness of the coloring pattern is shown in the column of "film thickness" in Table 17.

[Measurement of initial brightness]
The obtained coloring pattern is spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates in the XYZ color system of CIE using the characteristic function of the C light source. (X, y) and the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Light resistance evaluation]
An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by HOYA Corporation; cuts light of 380 nm or less) is placed on the obtained coloring pattern, and a light resistance tester (Suntest CPS +: Toyo Seiki Co., Ltd.) is placed. A light resistance test was carried out by irradiating xenon lamp light for 15 hours at (manufactured by Mfg. Co., Ltd.). When the stimulus value Y before the light resistance test (initial brightness obtained above) is 100%, the relative value (%) of the stimulus value Y after the light resistance test is the "brightness change rate" in Table 17. Shown in the column. The closer the rate of change in brightness is to 100%, the higher the light resistance.

Example 1-1
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 20 parts of the compound represented by the formula (I-1), and colorant (A): C.I. I. Pigment Yellow 138 2.2 parts of pigment composition, total amount,
Dispersant (BYK-LPN6919; manufactured by Big Chemie Japan Co., Ltd.) 26 copies,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate are mixed, and the compound represented by the formula (I-1) and C.I. I. A pigment composition consisting of Pigment Yellow 138 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 1-1.
A coloring pattern was obtained in the same manner as in Comparative Example 1 except that the comparative coloring curable composition 1 was replaced with the coloring curable composition 1-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 17.

Examples 1-2 to Example 1-60
The "colored curable composition" in Table 17 is the same as in Example 1-1, except that the compound represented by the formula (I-1) is replaced with the compound shown in the column of "XXXXX" in Table 17. The colored curable composition shown in the column was obtained, and a colored pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 17.

Example 1A-1
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): Compound 136, 20 parts, and Colorant (A): C.I. I. Pigment Yellow 138 2.2 parts of pigment composition, total amount,
Dispersant solution (solid content 60%) 26 parts,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate were mixed, and compound 136 and C.I. I. A pigment composition consisting of Pigment Yellow 138 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 1A-1.
A coloring pattern was obtained in the same manner as in Comparative Example 1 except that the comparative coloring curable composition 1 was replaced with the coloring curable composition 1A-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 18.

Example 1A-2 to Example 1A-231
Compound 136 is shown in the column of "color-curable composition" in Tables 18 to 21 in the same manner as in Example 1A-1 except that the compound 136 is replaced with the compound shown in the column of "XXXXX" in Tables 18 to 21. A coloring curable composition was obtained, and a coloring pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 18 to 21.

Comparative Example 2
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Pigment: C.I. I. Pigment Yellow 138 22 copies,
Dispersant 7.1 parts,
9.3 parts of the resin and 140 parts of the solvent (E): propylene glycol monomethyl ether acetate were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion liquid.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of pigment dispersion obtained;
Resin (B): 48 parts of resin B6 solution;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
11 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.7 copies;

重合開始剤（Ｄ）：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ−０１；ＢＡＳＦ社製） ４．５部；
密着促進剤:３−メタクリロキシプロピルトリメトキシシラン（信越化学工業（株）製）０．５７部；
溶剤（Ｅ）：４−ヒドロキシ−４−メチル−２−ペンタノン ８５部；
溶剤（Ｅ）：プロピレングリコールモノメチルエーテルアセテート ３３０部；及び
レベリング剤：ポリエーテル変性シリコーンオイル（トーレシリコーンＳＨ８４００；東レダウコーニング（株）製） ０．０９０部；を混合して比較着色硬化性組成物２を得た。

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; manufactured by BASF) 4.5 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.57 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 330 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); I got 2.

[Creation of coloring pattern]
The comparative color-curable composition 2 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a color-curable composition layer. .. After cooling, the distance between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used under an air atmosphere of 80 mJ / Exposure was performed with an exposure amount of cm ^{2 (based on 365 nm).} As the photomask, a photomask having a line-and-space pattern of 100 μm was used. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 70 seconds to develop and washed with water. This colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a colored pattern.
The film thickness of the obtained coloring pattern was measured using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.). The film thickness of the coloring pattern is shown in the column of "film thickness" in Table 22.

[Measurement of initial brightness]
The obtained coloring pattern is spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates in the XYZ color system of CIE using the characteristic function of the C light source. (X, y) and the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Light resistance evaluation]
An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by HOYA Corporation; cuts light of 380 nm or less) is placed on the obtained coloring pattern, and a light resistance tester (Suntest CPS +: Toyo Seiki Co., Ltd.) is placed. A light resistance test was carried out by irradiating xenon lamp light for 15 hours at (manufactured by Mfg. Co., Ltd.). When the stimulus value Y before the light resistance test (initial brightness obtained above) is 100%, the relative value (%) of the stimulus value Y after the light resistance test is the "brightness change rate" in Table 22. Shown in the column. The closer the rate of change in brightness is to 100%, the higher the light resistance.

Example 2-1
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 20 parts of the compound represented by the formula (I-1), and colorant (A): C.I. I. Pigment Yellow 185 2.2 parts of pigment composition, total amount,
Dispersant (BYK-LPN6919; manufactured by Big Chemie Japan Co., Ltd.) 26 copies,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate are mixed, and the compound represented by the formula (I-1) and C.I. I. A pigment composition consisting of Pigment Yellow 185 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

重合開始剤（Ｄ）：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ−０１；ＢＡＳＦ社製） ４．０部；
密着促進剤:３−メタクリロキシプロピルトリメトキシシラン（信越化学工業（株）製）０．５０部；
溶剤（Ｅ）：４−ヒドロキシ−４−メチル−２−ペンタノン ８５部；
溶剤（Ｅ）：プロピレングリコールモノメチルエーテルアセテート １１０部；及び
レベリング剤：ポリエーテル変性シリコーンオイル（トーレシリコーンＳＨ８４００；東レダウコーニング（株）製） ０．０９０部；を混合して着色硬化性組成物２−１を得た。
比較着色硬化性組成物２を着色硬化性組成物２−１に代える以外は、比較例２と同様にして、着色パターンを得た。また、初期明度の測定と耐光性評価を行った。結果を表２２における「膜厚」及び「明度変化率」の欄に示す。

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); Color curable composition 2 I got -1.
A coloring pattern was obtained in the same manner as in Comparative Example 2 except that the comparative coloring curable composition 2 was replaced with the coloring curable composition 2-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 22.

Example 2-2-60 Example 2-60
The "colored curable composition" in Table 22 is the same as in Example 2-1 except that the compound represented by the formula (I-1) is replaced with the compound shown in the column of "XXXXX" in Table 22. The colored curable composition shown in the column was obtained, and a colored pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 22.

Example 2A-1
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): Compound 136, 20 parts, and Colorant (A): C.I. I. Pigment Yellow 185 2.2 parts of pigment composition, total amount,
Dispersant solution (solid content 60%) 26 parts,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate were mixed, and compound 136 and C.I. I. A pigment composition consisting of Pigment Yellow 185 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

重合開始剤（Ｄ）：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ−０１；ＢＡＳＦ社製） ４．０部；
密着促進剤:３−メタクリロキシプロピルトリメトキシシラン（信越化学工業（株）製） ０．５０部；
溶剤（Ｅ）：４−ヒドロキシ−４−メチル−２−ペンタノン ８５部；
溶剤（Ｅ）：プロピレングリコールモノメチルエーテルアセテート １１０部；及び
レベリング剤：ポリエーテル変性シリコーンオイル（トーレシリコーンＳＨ８４００；東レダウコーニング（株）製） ０．０９０部；を混合して着色硬化性組成物２Ａ−１を得た。
比較着色硬化性組成物２を着色硬化性組成物２Ａ−１に代える以外は、比較例２と同様にして、着色パターンを得た。また、初期明度の測定と耐光性評価を行った。結果を表２３における「膜厚」及び「明度変化率」の欄に示す。

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); Color curable composition 2A I got -1.
A coloring pattern was obtained in the same manner as in Comparative Example 2 except that the comparative coloring curable composition 2 was replaced with the coloring curable composition 2A-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 23.

Example 2A-2 to Example 2A-231
Compound 136 is shown in the column of "color-curable composition" in Tables 23 to 26 in the same manner as in Example 2A-1 except that the compound 136 is replaced with the compound shown in the column of "XXXXX" in Tables 23 to 26. A coloring curable composition was obtained, and a coloring pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 23 to 26.

Comparative Example 3
Pigment: C.I. I. Pigment Green 58 47 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Pigment: C.I. I. Pigment Yellow 138 22 copies,
Dispersant 7.1 parts,
9.3 parts of the resin and 140 parts of the solvent (E): propylene glycol monomethyl ether acetate were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion liquid.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of pigment dispersion obtained;
Resin (B): 48 parts of resin B6 solution;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
11 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.7 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) 4.5 parts ;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.57 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 330 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a comparative color curable composition 3.

[Creation of coloring pattern]
The comparative color-curable composition 3 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to form a color-curable composition layer. .. After cooling, the distance between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used under an air atmosphere of 80 mJ / Exposure was performed with an exposure amount of cm ^{2 (based on 365 nm).} As the photomask, a photomask having a line-and-space pattern of 100 μm was used. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 70 seconds to develop and washed with water. This colored coating film was post-baked at 230 ° C. for 30 minutes to obtain a colored pattern.
The film thickness of the obtained coloring pattern was measured using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.). The film thickness of the coloring pattern is shown in the column of "film thickness" in Table 27.

[Measurement of initial brightness]
The obtained coloring pattern is spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates in the XYZ color system of CIE using the characteristic function of the C light source. (X, y) and the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Light resistance evaluation]
An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by HOYA Corporation; cuts light of 380 nm or less) is placed on the obtained coloring pattern, and a light resistance tester (Suntest CPS +: Toyo Seiki Co., Ltd.) is placed. A light resistance test was carried out by irradiating xenon lamp light for 15 hours at (manufactured by Mfg. Co., Ltd.). When the stimulus value Y before the light resistance test (initial brightness obtained above) is 100%, the relative value (%) of the stimulus value Y after the light resistance test is the "brightness change rate" in Table 27. Shown in the column. The closer the rate of change in brightness is to 100%, the higher the light resistance.

Example 3-1
Pigment: C.I. I. Pigment Green 58 46 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 21 parts of the compound represented by the formula (I-1), and pigment: C.I. I. Pigment Green 58 1. Total amount of pigment composition consisting of 1.1 parts,
Dispersant (BYK-LPN6919; manufactured by Big Chemie Japan Co., Ltd.) 26 copies,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate are mixed, and the compound represented by the formula (I-1) and C.I. I. A pigment composition consisting of Pigment Green 58 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 3-1.
A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative coloring curable composition 3 was replaced with the coloring curable composition 3-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 27.

Example 3-2 to Example 3-60
The "colored curable composition" in Table 27 is the same as in Example 3-1 except that the compound represented by the formula (I-1) is replaced with the compound shown in the column of "XXXXX" in Table 27. The colored curable composition shown in the column was obtained, and a colored pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 27.

Example 3A-1
Pigment: C.I. I. Pigment Green 58 46 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 21 parts of compound, and pigment: C.I. I. Pigment Green 58 1. Total amount of pigment composition consisting of 1.1 parts,
Dispersant solution (solid content 60%) 26 parts,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate were mixed, and compound 136 and C.I. I. A pigment composition consisting of Pigment Green 58 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 3A-1.
A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative coloring curable composition 3 was replaced with the coloring curable composition 3A-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 28.

Example 3A-2 to Example 3A-231
Compound 136 is shown in the column of "colorable curable composition" in Tables 28 to 31 in the same manner as in Example 3A-1 except that the compound 136 is replaced with the compound shown in the column of "XXXXX" in Tables 28 to 31. A coloring curable composition was obtained, and a coloring pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 28 to 31.

Example 3B-1
Pigment: C.I. I. Pigment Green 58 46 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 21 parts of compound, and pigment: C.I. I. Pigment Green 59 1.1 parts of pigment composition, total amount,
Dispersant solution (solid content 60%) 26 parts,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate were mixed, and compound 136 and C.I. I. A pigment composition consisting of Pigment Green 58 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 3B-1.
A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative coloring curable composition 3 was replaced with the coloring curable composition 3B-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 32.

Example 3B-2 to Example 3B-231
Compound 136 is shown in the column of "colorable curable composition" in Tables 32 to 35 in the same manner as in Example 3B-1 except that the compound 136 is replaced with the compound shown in the column of "XXXXX" in Tables 32 to 35. A coloring curable composition was obtained, and a coloring pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 32 to 35.

Example 3C-1
Pigment: C.I. I. Pigment Green 58 46 copies,
6.4 parts of acrylic pigment dispersant,
A pigment dispersion (colorant (A2) -containing liquid) in which 57 parts of a resin (B): a resin B5 solution and 220 parts of a solvent (E): propylene glycol monomethyl ether acetate were mixed and the pigment was dispersed using a bead mill. Prepared. Separately
Colorant (A): 21 parts of compound, and pigment: C.I. I. Pigment Green 7 1. The total amount of the pigment composition consisting of 1.1 parts,
Dispersant solution (solid content 60%) 26 parts,
Resin (B): 44 parts of resin B1 solution and solvent (E): 350 parts of propylene glycol monomethyl ether acetate were mixed, and compound 136 and C.I. I. A pigment composition consisting of Pigment Green 58 was dispersed to obtain a colored composition.
Then
Total amount of the obtained pigment dispersion liquid (colorant (A2) -containing liquid);
Total amount of the obtained coloring composition;
Resin (B): Resin B6 solution 8.3 parts;
Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
9.9 copies;
Polymerization initiator (D): Compound represented by the following formula (manufactured by Changzhou Powerful Electronic New Material Crotch Co., Ltd.)
5.0 copies;

Polymerization Initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure® OXE-01; BASF) 4.0 parts;
Adhesion accelerator: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.) 0.50 parts;
Solvent (E): 85 parts of 4-hydroxy-4-methyl-2-pentanone;
Solvent (E): 110 parts of propylene glycol monomethyl ether acetate; and leveling agent: 0.090 parts of polyether-modified silicone oil (Torre Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.);
Was mixed to obtain a colored curable composition 3C-1.
A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative coloring curable composition 3 was replaced with the coloring curable composition 3C-1. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Table 36.

Example 3C-2 to Example 3C-231
Compound 136 is shown in the column of "colorable curable composition" in Tables 36 to 39 in the same manner as in Example 3C-1 except that the compound 136 is replaced with the compound shown in the column of "XXXXX" in Tables 36 to 39. A coloring curable composition was obtained, and a coloring pattern was obtained. In addition, the initial brightness was measured and the light resistance was evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 36 to 39.

From the above results, the light resistance was improved in the coloring pattern formed from the coloring curable composition containing the pigment composition of the present invention.

Since the pigment composition, coloring composition and coloring curable composition of the present invention can be used for forming a color filter having improved light resistance, they are suitably used for display devices such as color filters and liquid crystal displays. ..

Claims (14)

The compound represented by the formula (I) and
Quinophthalone compound and isoindoline compounds other than the compounds represented by formula (I) or green colorant seen including,
A pigment containing at least one compound selected from the group consisting of a compound represented by the formula (Ia) and a compound represented by the formula (Ib). Composition.

[In formula (I), L ¹ represents −CO− or −SO _2−.
R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
R ¹¹ and R ¹⁰¹ represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.
The wavy line represents an E-body or a Z-body. ]

[In the formula (Ia), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
L ² represents −CO − or −SO _2−.
R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. ]

[In the formula (I-b), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ²⁰ and R ³⁰ combine to form a ring Q.
The ring Q may have a substituent and has 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocycle. A single ring having 5 to 7 ring members or a condensed ring obtained by condensing the single ring, which is selected from a hydrocarbon ring and a heterocycle, may be bonded to the ring Q. ] The pigment composition according to claim 1 , wherein in the formula (Ia), R ¹¹ and R ¹⁴ are the same group, and L ¹ and L ² are the same group. In formula (Ia), R ¹¹ and R ¹⁴ are independent of each other, an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, and a substituent. A naphthyl group which may have a group, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a frill group or a substituent which may have a substituent. The pigment composition according to claim 1 or 2 , which is a pyridinyl group which may have. Compounds of the formula (I -b) is a pigment composition according to claim 1 which is a compound represented by formula (I-c).

[In the formula (I-c), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ⁶ and R ⁷ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO _2- R ^101. , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ , -NHCOOR ¹⁰² , -OCON ( R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group or a substituent having 1 to 40 carbon atoms which may have a substituent. Represents a good heterocycle.
R ¹⁰¹ , R ¹⁰² and M have the same meanings as described above. ] The pigment composition according to any one of claims 1 to 4 , wherein R ¹ is a hydrogen atom and R ^{2 to} R ⁵ are hydrogen atoms or nitro groups independently of each other. A coloring composition containing the pigment composition and solvent according to any one of claims 1 to 5. The coloring composition according to claim 6 , further comprising a resin. The coloring composition according to claim 6 or 7 , further comprising a compound represented by the formula (I), a yellow colorant or a green colorant. A coloring curable composition containing the coloring composition according to any one of claims 6 to 8 and a polymerizable compound. The color-curable composition according to claim 9 , further comprising a polymerization initiator. A color filter formed from the coloring composition or the coloring curable composition according to any one of claims 6 to 10. A liquid crystal display device including the color filter according to claim 11. The compound represented by the formula (I) and
A pigment composition containing a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), or a green colorant, a solvent, and a colorant (A2) -containing liquid containing the colorant (A2) and the solvent. A method for producing a coloring composition to be mixed.
Production in which the compound represented by the formula (I) contains at least one compound selected from the group consisting of the compound represented by the formula (Ia) and the compound represented by the formula (Ib). Method .

[In formula (I), L ¹ represents −CO− or −SO _2−.
R ^{1 to} R ⁵ and R ^{12 to} R ¹³ are independent of each other, hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -O-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON (R ¹⁰² ) ₂ , -N (R ¹⁰² ) ₂ , -NHCO-R ¹⁰² , -NHCO-N (R ¹⁰² ) ₂ ,- NHCOOR ¹⁰² , -OCON (R ¹⁰² ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, hydrocarbon group or substitution with 1 to 40 carbon atoms which may have a substituent. Represents a heterocyclic group which may have a group.
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ , respectively, may be coupled to each other to form a ring.
R ¹¹ and R ¹⁰¹ represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent independently of each other.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When ^{there are a plurality of R 101} , R ¹⁰² and M, they may be the same or different.
The wavy line represents an E-body or a Z-body. ]

[In the formula (Ia), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
L ² represents −CO − or −SO _2−.
R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. ]

[In the formula (I-b), L ¹ , R ¹¹ , R ^{1 to} R ⁵ and the wavy line have the same meanings as described above.
R ²⁰ and R ³⁰ combine to form a ring Q.
The ring Q may have a substituent and has 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocycle. A single ring having 5 to 7 ring members or a condensed ring obtained by condensing the single ring, which is selected from a hydrocarbon ring and a heterocycle, may be bonded to the ring Q. ] The production method according to claim 13 , wherein the colorant (A2) is one or more colorants selected from a compound represented by the formula (I), a green colorant, and a yellow colorant.